October 24, 2022

Brand Building and Public Relations for Travel Insurance Tech: Don’t spray and pray (podcast episode #36)


Get ideas for public relations, remote work, and the minimum viable product by listening to episode #36 of the How I Made It In Marketing podcast. I had a passionate conversation with Lauren Gumport, VP of Communications & Brand, Faye.

Listen now to hear Gumport discuss when things go wrong, the first iteration of the product, and work/life balance.

by Daniel Burstein, Senior Director, Content & Marketing, MarketingSherpa and MECLABS Institute

Brand Building and Public Relations for Travel Insurance Tech: Don’t spray and pray (podcast episode #36)

This article was published in the MarketingSherpa email newsletter.

“Remember the prospect is a person. Do not talk AT them; talk TO them,” Flint McGlaughlin taught in Above-the-Fold Psychology: How to optimize the top 4 inches of your webpage.

I asked our latest guest how she keeps the focus on the prospect as a person, and she shared examples ranging from A/B testing of CTA buttons to picking the brains of the person sitting next to her on an airplane.

Listen to my conversation with Lauren Gumport, VP of Communications & Brand, Faye, using this embedded player or click through to your preferred audio streaming service using the links below it.

Listen on Apple Podcasts | Listen on Spotify | Listen on Google Podcasts

Gumport began her career in PR in New York City, working at global agency Ketchum on clients including MasterCard and Nestle. She then moved abroad to Tel Aviv and transitioned out of corporate America and into the startup scene. Her roles included:

  • PR & Content Marketing Manager at Matomy Media Group
  • Director of Communications at Playbuzz
  • Director of Global Communications & Brand Strategy at Guesty
  • And now… VP of Communications & Brand at Faye, a travel insurance startup

Gumport has managed teams of 10+ and million-dollar budgets and has over a decade of experience in launching high-growth startups to global audiences.

Faye has pulled in $8 million in a seed-funding round led by Viola Ventures and F2 Venture Capital. Also participating was former NBA player Omri Casspi. The team is made up of travel and insurance pros, with several folks coming from Allianz, as well as the VP of Growth hailing from Lemonade. Gumport herself has specialized in travel for years, after spending the last few at Guesty, a company that provides software to Airbnb hosts to automate their operations.

Asked about what her day is like at Faye, Gumport said:

“Every day is different, which I very much enjoy. We’re at the beginning – we launched earlier this year after building Faye travel insurance during COVID, we then announced our seed funding and soon after we were named a must download travel app by Fodor’s. So, things are moving quickly, and we’re shaking up a sleepy space, overdelivering when many legacy players are doing the opposite.

This means we’re super focused on building trust and credibility, so travelers get to know us, have confidence in our product and continue to adventure with Faye.

This means investing in getting our name out there – through organic PR efforts as well as paid marketing efforts. This means going above and beyond to provide a top-notch experience for those traveling with Faye

And this means investing in our brand – for example, the travel insurance copy you read on our website is not confusing jargon mumbo jumbo. You actually know what you’re protected for when you purchase a Faye policy.”

Stories (with lessons) about what she made in marketing

Some lessons from Gumport that emerged in our discussion:

Take others' suggestions into account, with the understanding that you're the pro in your field and have the final say.

Gumport works in PR and fields suggestions from coworkers all the time on what would make a good story. Many ideas are great, but whether they are newsworthy is an entirely different ball game. Learn to set expectations on what results are realistic, take suggestions gracefully, but go with your gut as to what will help you meet your KPIs and get your company where it needs to be.

For those that don’t work in PR, any exciting update can seem “newsworthy” to them. But let’s be real, reporters don’t care about your latest app update or the new widget you released, Gumport says. That’s not news, though its super exciting for you and your company.

A newsworthy moment is what audiences would truly love reading – maybe it’s a feel-good story about your customers, many times it’s thought-provoking thought leadership commentary and MOST of the time it’s data-driven stories that speak to a current trend. For example, that could be the percentage of Americans looking to travel – or hold back on travel – given America’s current economic outlook.

The #1 moment in time that is super hard to set expectations in is when it comes to funding news. You can’t just snap your fingers and get a TechCrunch story. It doesn’t work like that – everyone is receiving funding! You must point out why you’re different, what pain points you’re solving, why your investors and advisors are interesting, and so on.

Gumport will never forget at Playbuzz, the first startup she worked for in Tel Aviv, when Disney invested in the company. They weren’t the LEAD investor, but they were the most interesting, so the team led with that, and it resulted in a TON of top-tier press. Uncover what drives the story, and never make your story a sale pitch.

She also seeks feedback from customers. Lucky for her, being in travel, most people you meet nowadays are travelers – travel is no longer a luxury, it’s a right, she says. So, she gets to ask her family, her friends, anyone she meets really, for feedback on Faye Travel Insurance – purchase flow, product, message, and so on.

Understanding how those who have purchased travel insurance in the past feel and what messages they want to see (mainly it’s about quick claims reimbursements) versus how those who have never purchased it in the past react to messaging, this feedback is super helpful in how the startup approaches customers.

However, we’re not always a pro in everything. Gumport’s advice when you’re not a pro…

Ask for help, always. Identify the individuals who you feel can guide you in this area. You want to develop a relationship and reach out to them – cold messaging on LinkedIn is completely appropriate. Lean on friends of friends who are professionals in their field – rarely has she ever been told “no” if she has asked for a meeting where she is seeking someone’s advice or guidance. Nine times out of 10, people are happy to help and give you their time.

When it comes to building your career, she always suggests people start with LinkedIn. Now that may sound basic, but hear me out, Gumport says. During COVID, she made a goal for herself to invest more of her time in LinkedIn. She did PR for others – it was time she did some for herself.

The end result: she got her current job from LinkedIn – that’s how she connected with the person who originally interviewed her, who saw all her content about travel. And voila, she is now at her second travel startup.

For those not investing time in LinkedIn yet – set aside 30-45 minutes per week; connect with others, comment on posts, write your own. The more you put into it, the more you get out of it.

Being successful doesn't correlate with how many hours are spent in the office nor does it mean compromising on your work/life balance.

Gumport is a huge proponent of being efficient, especially during office hours, in order to have a personal life. This doesn't mean sitting in your desk chair until 6PM if you have nothing to do. If you meet your KPIs and get your work done, focus on yourself – health and wellness is key to being successful.

She thinks this mindset is really applicable to today’s work environment, with hybrid schedules and for many still, the ability to work remotely.

She is constantly working in different countries and as long as she is meeting her goals and she is online when her team is online, she lets herself explore in her downtime.

Showing up at an office every day and being chained to a desk, waiting for the clock to strike 6PM, does not equate to success. Meeting, and exceeding, your KPIs does.

She also makes sure that people naturally see her successes. For example, 4.7/5 on Trustpilot was a goal for the startup. When they reached it, they shared it in real time on Slack with a GIF. It excites employees and then they want to share the news which then helps the company with hiring.  

Just because others don't get it, it doesn't mean you should stop.

Gumport is hard to manage because she wants to work remotely much of the time, from everywhere in the world. But for some, a significant office presence matters. This has put her in uncomfortable positions with managers in the past, who acknowledge her successes but still prefer she is not remote as much as she'd like to be. At a certain point in your career, you need to do what's right for YOU and what will result in the most productivity, she advises. Pick an office culture that fosters what works for you.

Gumport has definitely been managed by people who count to the minute when you’re in the office and that’s just no way to live, she says. Shop for a manager who understands how you best work and promotes flexible working habits and a work/life balance.

Don’t get me wrong, Gumport says, there are sometimes crises and that means putting in hours in your off-time. And that’s just reality – especially in startup life. But that’s not 24/7.

She came to a point in her career where she knew her value, and how she works best, and she just didn’t want to compromise. It was exhausting for her being concerned how others couldn't understand how she could work remotely from a different country nonstop. She finds that mindset very old school, and companies that don’t evolve will be left behind with talent that doesn’t want to work for those who haven’t adopted more flexible working policies.

So that said, the best office culture for her is the one she has now – in the office a few days a week, and sometimes remote when she chooses, with a manager who understands she is trustworthy and can provide results from anywhere.

Here are Gumport’s tips for working remote:

  • all video calls are with the camera on
  • always overlapping on time zone
  • weeklies with her boss and her direct reports
  • and she overcommunicates

This lesson – just because others don’t get it, doesn’t mean you should stop – has to apply to marketing and content as well, of course.

Gumport thinks the best way to build good copy is to start with understanding consumers' pain points, and how what you’re selling is the solution. Go from there. Understand what the consumer wants. This specifically applies to PPC ads on Facebook, etc.

For example, in travel a major pain point can be lost bags, especially right now. And what do consumers want? Peace of mind that they won’t lose their luggage (hello AirTags) and if they DO, understanding that they’ll be reimbursed quickly so they don’t have to pay out of pocket.

When she is writing an op ed or pitch, Gumport tends to start with the headline first to grab the attention of those reading from the get-go.

Stories (with lessons) about the people she made it with

Gumport also shared lessons she learned from the people she collaborated with:

When things go wrong, it's an opportunity.

via Elad Schaffer, CEO, Faye

After Gumport lost phone access in a water-related incident and was cell-less for 24 hours, she freaked out that she was unavailable and was uber apologetic afterwards. “It’s completely fine; it was an opportunity,” Schaffer said afterwards. And he was right. She used that time without a phone to craft a strategy for becoming a mission-driven company. She found herself inspired and less distracted, which ultimately led her to taking time to write and read more frequently with her phone in a different room.

Gumport says she has an amazing boss who also plays therapist when she is stressed. She’s very lucky to work for someone who has such a great perspective on everything. And when she was phone-less, she was able to set herself outside, in nature, and craft a strategy for Faye to be a mission-driven company that powers positive adventures worldwide.

Don't spray and pray.

via Parry Headrick, Founder, Crackle PR

Gumport is in PR, so advice on media relations is always appreciated. Headrick always says don't spray and pray – meaning: you can't send reporters the same pitch over and over again. Customize pitches to reporters who actually write about the topics you're covering. He couldn't be more right – and this approach has helped her secure top-tier coverage for the companies she works for.

Gumport encourages marketers and entrepreneurs to follow Headrick on LinkedIn if you want a crash course in PR. He’s incredible, funny and brutally honest, she says.

When it comes to earning media, Gumport has been featured in USA Today, BuzzFeed, The Wall Street Journal, TripSavvy and more because she has pitched reporters with timely commentary, such as holiday travel tips, or how to travel smart amid inflation.

She also got an FT (Financial Times) story once because she told the reporter that one of the investors at the company she was working at loved it so much that they took an office in the company’s office – that got them the story.

If you're not embarrassed about the first iteration of the product you put out, then you're doing it wrong

via Dan Green, Co-founder & CTO, Faye

When launching Faye, Green told the team this lesson. They wanted many more capabilities and more copy live before launch but they had to meet their deadline of going live. And he was right – it was OKAY, more than okay. And after they went live, they updated copy and have continued to evolve their person-first, digital travel insurance offering. You can't be perfect when you launch a product, and you shouldn't be seeking perfection. Seek product-market fit.

Green is not only a brilliant leader, he has also traveled the world 43 times, and this is not his first startup.  Green and Schaffer (her boss, the CEO, who is the other cofounder of Faye) founded a company previous to Faye.

The team knew they had product-market fit and they needed to go live, especially with the keen interest in trip protection following a couple years of COVID resulting in money lost over tickets and such.

Gumport will never forget Green saying, “sometimes, everything doesn’t have to be perfect!”

The key qualities of an effective marketer

At the end of the episode, Gumport discussed the key qualities of an effective marketer. She said you need to know when to pump the brakes on selling and focus on the needs of the greater community and your target audience. Empathy is currency, which was incredibly true during the height of COVID and any other unique time period that is difficult to navigate.

She said you need to be a good writer, be scrappy, pivot fast, and think and plan ahead.

Related content mentioned in this episode

Marketing Career: What you need to understand at each step of the job seeker’s journey (even if you’re not looking)

Does Your Marketing Copy Have Earfeel?

About this podcast

This podcast is not about marketing – it is about the marketer. It draws its inspiration from the Flint McGlaughlin quote, “The key to transformative marketing is a transformed marketer” from the Become a Marketer-Philosopher: Create and optimize high-converting webpages free digital marketing course.


Not ready for a listen yet? Interested in searching the conversation? No problem. Below is a tough transcript of our discussion.

Daniel Burstein: I get a lot of PR pitches for Marketing Sherpa, a heck of a lot. That's a nice way to say it. And here's the biggest flaw in most of the pitches I see, they are focused on themselves. It might literally be themselves for some people doing their own pitching, but mostly it's PR pitches focused on their message or their product, whatever their client is trying to, for lack of a better word, shill.

But then among all that there are those beautiful golden needles in a haystack that put the Marketing Sherpa audience first. That focus on what value they can bring to our audience, whether through our written case studies or for guests right here on the How I Made It In Marketing podcast. So when I read this lesson about PR in a podcast guest application, it resonated with me right away.

Don't spray and pray. We'll hear the story behind that lesson, along with many more lesson filled stories from Lauren Gumport, VP of Communications and Brand at Faye. Thank you for joining us, Lauren.

Lauren Gumport: Thanks for having me.

Daniel Burstein: Alright,  so I'm going to look at your background real quick, cherry picking from your LinkedIn here. You started as an Account Executive at Ketchum where you worked on MasterCard, Nestlé, Obamacare. Ah, you were Director of Communications at Playbuzz, Director of Global Communications and Brand Strategy at Guesty. You've managed teams of ten +, you've managed million dollar budgets and right now you are VP of Communications and Brand at Faye.

I’ll tell people who Faye is real quickly. Faye has pulled in $8 million in a seed funding round led by Viola Ventures and F2 venture capital. It also had participation from former NBA player Omri Casspi, which is super cool. So give us a sense, what is your day like as VP of Communications and Brand at Faye?

Lauren Gumport: Yeah, so I mean every day is different, which I really like. We're at the beginning, you know, we launched earlier this year, we built Faye Travel Insurance during COVID. We then announced our seed funding and things are moving so quickly. You know soon after we were named this months download travel app by Fodor's travel. And this means because we're a new brand in really an ecosystem that is dominated by legacy players I would say. We're focused on building, you know, trust and credibility. So travelers get to know us so they get to know what travel insurance should be. So they have confidence in our product. And so they continue to travel with us, of course. And this means a lot of time spent investing in our brand.

For example, you know, the travel insurance copy that you read on our website it’s not confusing jargon or mumbo jumbo. You actually know what you're protected for when you purchase a Faye policy. And creating copy about travel, insurance is no easy feat. If you're in the insurance ecosystem you know this so it takes quite a bit of time.

Daniel Burstein: Well, before we get into your specific stories, that just piques my ears because how did you work with the legal team in compliance and whoever? Insurance must be a really difficult product to not have too much mumbo jumbo for. I've worked in real estate. I've written radio ads for a major car brand I won't mention, and the radio ads are so frustrating. It's like a 32nd spot and 10 seconds where, you know, the speed reading of some, you know, compliance. So, any tips there for working with your  legal friends to make that happen?


Lauren Gumport: I would say patience and a glass of wine at the end of the day. No, you know, insurance and compliance go hand in hand. And, you know, Faye really want to do things differently in terms of how we talk about travel insurance and how we approach it. And that can be really scary for those who've been in the industry for a long time and aren't used to that. So I would say it's a lot of patience, it's a lot of iterations. It's making sure that everything is factually correct but easily digestible to consumers, to travelers.

Daniel Burstein: All right. Well, we're going to unpack some lessons from your current role, your previous roles. Let's jump into it and let's look at some lessons you've learned from your career, from the things you made in marketing. Your first lesson is, take other suggestions into account with the understanding that you're that pro excuse me, let me try that again. Take others suggestions into account with the understanding that you're the pro in your field and have the final say. So Lauren, how did you learn this lesson?

Lauren Gumport: I mean, I'm always asking people for help and I'm kind of like a frequent question asker in general. And, you know, lucky for me, in the field I am in now, which is travel, and most people that you meet nowadays are travelers, right? Travel is no longer a luxury it's a right. So when it comes to, you know, Faye product copy or the purchase process or the website or, you know, creating an iteration of the website before launch, I get to ask my friends, I get to ask my family. I really get to ask anyone I meet about their feedback. And then it's about, you know, kind of even putting people mentally into little focus groups. Like for me, it's people who have traveled with travel insurance before and people who haven't and what messages resonate with them and make them want to purchase your product.

Daniel Burstein: So I've had some of the best advice from just people I've sat next to in a plane. You know, when you find out what they do, pick them. You're sitting there with them for a few hours. So you're on a plane and you're like, you know, Hey, you got some good travel insurance there, is this trip insured. And are you like, just picking at different people you meet?

Lauren Gumport: Yeah, yeah, for sure. I mean, I would say that, like, I'm a talker and I could talk to a wall. So I was recently remote for, you know, a month traveling and working remotely at the same time. So I constantly was asking everyone, including the people who checked me in at the hotel, if they could check out our app and let me know what they think is working and what's not working.

Daniel Burstein: So I also wonder how getting suggestions from others like helps you better understand the customer. Like when you're in that conference room, when you're debating with the CTO or the CEO or whoever about what approach you're going to take, are you able to like pull in those stories into that conversation. And I'll tell you why.

So we've got a free digital marketing course and in the above the fold psychology section Flint McGlaughlin teaches, remember the prospect is a person do not talk at them talk to them. And so important to remember the humanity of the people on the other side. Because we've got these databases, these CRMs, these email platforms, analytics numbers, numbers, numbers. But there's actually a human being. So have you ever been able to, like, pull into the you know, the company wants to take it one direction. You're like, well, look, I was sitting next to Bobby on the plane and he, you know, get a sense of like bring that in and help you win the battle, so to speak.

Lauren Gumport: Oh, for sure. I always do it with data, though, so I will always take a data driven approach to any type of argument I go into a meeting about. And so there are, for example, you know, we could be everybody could be a fan of creating a CTA button that says Get your trip covered or get covered. And really, when we test CTAs we did an A/B test on the website and drive X amount of traffic towards one. And check pricing or get a quote, which maybe aren't as fun, but they're working and they're converting more. So I am always going to go into a discussion and a disagreement with numbers to back up my argument.

Daniel Burstein: That's perfect we're big fans of A/B testing. I also wondered, so you talk about when you're a pro you know a lot of marketers experiences I used to have a boss who joked like, hey, do you think the like CTO ever gets the CEO coming in the office and say, Hey, I was thinking last night about some new way to do our JavaScript or you know, and me like they usually don't get that us marketers. Everyone thinks they know how to do marketing, so everyone in the organization's like they got this idea. They got that idea. But in fairness, right, there's areas where we're not a pro. And I wonder, like, how do you work with your colleagues to get ideas there for the marketing or for the technology? A very technology driven company.

So for me, you know, I had written an article for Marketing Sherpa about the job seekers journey and, you know, how to reach out to all these H.R. folks and all because it was yeah, it was about marketing because it was for marketers a job seekers journey. But I've been here 13 years, it's been a long time since I’ve looked for a job. So I was like, let me reach into the H.R. field and see what we can learn from them. So how do you do that? How do you collaborate with others? CTO, CIO, H.R whatever when you're not a pro?

Lauren Gumport: Well, I will say that as a marketer and I think, you know, I've had this said to me so many times, but when you are speaking with a non marketer who just wants their product to succeed and they say to you, Hey, we have to make something go viral, I just, I just I can't handle it, and I understand, of course we want to, I can't even say the V word, but you know what I mean. Of course we want something to go schmiral let’s just say schmiral. But it doesn't just happen because you're creating this idea in a room, right? It happens because you snag on to something in the news cycle and it happens from, you know, creating smart narratives around something that consistently grow. And, you know, so I definitely find that setting expectations used to be very hard for me when I was younger, like five years ago, I could not set people's expectations. I was very much a yes person, which helps nobody.

You have to set people's expectations so they understand what type of results that you're going to get them and how and educate them on how you're going to do so. For example, a PR pitch does not mean a sales pitch about your product. It means providing thought provoking commentary and data driven statistics about a timely topic.

For me when I need help on a topic that I'm not a pro and I will cold email people, I will ask my friends for friends that they have who are professionals in the areas that I need help in. And nine times out of ten, those individuals will always sit and meet me for a coffee. All it costs is their time.  It's only done good things for me I would say. When it comes to like building your career, I know we kind of spoke about this. You know, if I can offer suggestions for people, it's first of all, speak to those individuals, grow your network and this is going to sound super lame and Im’ going to say, anyway, invest time in LinkedIn. And really I'm saying like 30 to 45 minutes a week in LinkedIn, widening and broadening your network, connecting with professionals who can help you in areas that you're not a pro in. LinkedIn got me my job, my current job I got from LinkedIn because those hiring at my company noticed my posts about travel. And of course now I work at a travel company.

Daniel Burstein: So I'm really introverted. You're saying cold emailing like what are you putting in that, you know, like what's the value exchange? What are you offering? Like, how are you doing that reach out. I mean, I also say I get endless pitches from people, so I'd imagine like you really got to stick out in that inbox.

Lauren Gumport: Yeah. I mean, I'm pretty casual like before, so it's like I will cold LinkedIn message so many people like hey Jessica saw your awesome post on X topic. I'm looking for a mentor in x area and I would really love to meet with you to talk about this topic. Are you free? I'd love to treat you to coffee and just take 30 minutes of your time. And if you can have not just in person,  I've had virtual phone calls from the people that I've connected with on LinkedIn. And we talk probably like once every few months now.

Daniel Burstein: Wow, that's great. All right. Here's our next lesson from Lauren. Being successful doesn't correlate with how many hours are spent in the office, nor does it mean compromising on your work life balance. So I read this. I want it to be true, Lauren. I want it to be true. But I know I work remotely now. Having worked in an office it tends to be the people that are there like burning the midnight oil or come in early. Like, they seem like they're doing so well, you know what I mean? If you're like the CMO, if you're leading the organization, like, oh, look at all the work they're putting in. And it's a lot harder to see the effectiveness of that work. So how do you kind of overcome that? You know, butts in seats mentality.

Lauren Gumport: Yeah, I mean, I disagree. It's there is so much value in being in person. First of all, by the way, interpersonal relationships, creating a culture, there is a lot of value to time spent in an office. What I'm saying is that there is no reason today in today's work environment that you should be required to be in office 9 to 5 9 to 6 every day just because that's what the company wants, right. I think that that does the opposite of what it's supposed to. I think that fosters actually a bad culture. Because in today's environment, working remotely and hybrid schedules and flexibility, they're top of mind for top talent. So if you want top talent, you need to evolve as a company. When I see these companies that are kind of like going backwards and they have remote, flexible policies during the height of COVID, and now they're saying, Oh, wait, actually everyone should come back into the office.It creates a lot of resentment and you're going to lose talent, right?

Not to mention, being in the office is super social, so that's incredible for culture. But am I more productive in the office or when I'm working remote? When I'm working remote 100%.  I'm in communications and marketing. I'm writing all day. And so I don't believe that full time in the office equates to success and I think it actually equates to misery, frankly.

Daniel Burstein: Well, let's talk about working remote in just a moment, but I think you make a good point here about, you know, it's easy, again, as leader to look around and see who's burning the oil, who's staying in the office. And those are the ones that are successful. Like you have an example, I think you mentioned Trustpilot of how you can communicate to your organization in organic way. Hey, the things we're doing are working. Even if you don't see me at the office at 10:00 at night.  

Lauren Gumport: For sure. So, you know, I'm an over communicator in general. So I think that merchandizing your wins internally is super key. We are a Slack company. If you are a Slack company, you know what that means? That we're very little email, etc. So whenever we get any type of media attention or new partnership, new hire, you know, celebratory moment, it is shared on Slack in the relevant Slack channel.

So with Trustpilot, you know, a review site, we had a goal to get to 4.7 out of five within six months of launching. We met that goal. We were super excited. So in real time, of course, I'm sharing that with the team. I'm providing them with suggested copy that they can share in their own personal social channels. They don't have to, but we're making it this celebratory moment. It makes everybody want to organically share this with their communities. And then in turn, it just helps us with hiring because everyone is seeing all of their friends, all their connections, posting about this great achievement of ours in such a short time. Then it helps with recruitment. So I would say transparency, sharing your results in real time with the whole team is super key.

Daniel Burstein: That's great. I think the other thing, you know, so like I said,  from when I started my career at an agency, it was definitely that butts in seats mentality, who's coming in the weekend whose working late at night and all that stuff. But I think the thing where I struggle with that there is I hate working on the last second on deadlines. I  know some people get the energy from it. Oh, we're up against deadlines. I'm always working ahead, I'm always thinking ahead of our deadlines. That's how we consistently publish in Marketing Sherpa. And so when I would see people, like oh they got to work every week and working late it’s because they weren't planning. Well, like you said, they're walking around the office or talking at the water cooler or bs’ing all day.

Lauren Gumport: Be efficient.

Daniel Burstein: Be efficient, yeah. I mean, for us, you know, I started publishing print ads and so the deadline was well it had to get to the publication a certain time. And then the deadline was, well FedEx picked up at a certain time. But here's the thing they figured out, well, FedEx picked up at our office a certain time at the local FedEx office a certain time, and at the airport even later, so they would push the deadline back to like we'll even drive it to the airport.

So also I would encourage any leader who's got that mentality, also look is someone not working those late hours because they're efficient, and they’re planning well, and they’re not going around.

Lauren Gumport: I have to say that I think it's just so funny because if I give a deadline for a project that I assign to someone on my team and I'm like, Tuesday, end of day, if I'm getting that at Tuesday at 11 p.m., it means that you didn't use the work hours where of us were online at the same time in the most efficient way possible and I'm not going to review that tonight. Like I'm going to review that tomorrow. And if it's a weekend, I'm not going to review it. So, yeah, I hear what you're saying.

Daniel Burstein: All right. Well, let's talk about that. Working remotely bit. And I think you said here, just because others just don't get it, it doesn't mean you should stop. So what did they get and why did you push forward?

Lauren Gumport: You know, I think that because working remotely is now more widely adopted and accepted. There was a time pre-COVID where it wasn't you know, we knew digital nomads that, but they weren't, you know, so prevalent as they are today, right. So I would go to work remote, you know, and it was agreed upon with my boss. And then other people are kind of wondering, who are not on my team. Oh, she's always on vacation. What are you talking about? What do you mean? I'm on vacation? I'm working from a different country. Just because I'm not physically in the office doesn't mean I'm not working. And I find that mindset so archaic and so old school and I'm like, turning red. It makes me so frustrated.

And at a certain point, I just thought to myself, I have to stop caring about what other people think about my work arrangement because I get the results. I've proven my value and it's working between me and my manager and for the company. So, it was more a mindset I probably had to change about myself. And a lot of people also can't always work remotely. You know, you have kids in school or family members you have to take care of. So there was also kind of like this level of, oh, well, she can do it, but I can't. And that's also frustrating, you know, so I'm just trying to live Daniel.

Daniel Burstein: We’re all trying to figure this out. But all right, let me challenge you there a bit, because we're marketers, right? So you say, like, I don't care what everyone else thinks about. What we do is perceived value. What customers think about or what our partners think about what we do as marketers is we shape perceived value so they can see that the actual value we create, they can perceive it.

So what are some things you've done to help your leaders, your peers, whoever you're working with, to see their perceived value of the work you're putting in as a remote employee? Because I would assume you maybe had to go a little extra mile to communicate that value. Then when you were working in the office, what are some things you've learned?

Lauren Gumport: I'm an over communicator for sure. You know, any type of meeting. It's always video. If I am remote video camera on 100%, I'm always overlapping on time zones, so maybe that means starting work way earlier or starting work way later or just frankly being available, you know, throughout the day, just on Slack, email, WhatsApp, etc., making myself available. Frequent check ins.Obviously Weekly is with my boss and my direct reports. It's just being in touch, constant communication, building trust between not just you and your boss and you and those on your team, but everyone at the company. So they understand if I'm not physically there, but I send her message, she's completely responsive.

If I had someone on my team who wanted to work remote and we had it worked remote, you know, together before I said, okay, let's do a trial. Let’s do a trial and see how this goes. If I found that they were not responsive, that they weren't overlapping on time and that they didn't meet their KPIs, then they would not be allowed to work remotely. You can work remote if you're producing results, if you're meeting and exceeding your expectations, and if you're a high performer and that's how it should be. You shouldn't be working remote because you want to do whatever you want to do it’s a job. It's still a job.

Daniel Burstein: So how do you apply this lesson? The lesson just because others don't get it doesn't mean you should stop to your marketing and content, right? So like for me, I've written before about making sure your copy has your feel. It isn’t just fact based stuff, like a value prop. It's more subjective. It's not the function of the creative, it's the form and when they hear that form, you need the function too, you need the actual information. But when that right audience member, that ideal customer hears that right form, then they will get it. They won’t get it at first, but when the hear it the right way for them, then they will get it.  So, this is a great lesson, just because others don't get it doesn't mean you should stop. How do you apply that to your marketing and your content?

Lauren Gumport: I think you need to try to nail copy that people are already thinking, right? So it's like they were thinking it they just didn't put it in words. And for some reason your copy represents exactly what they were thinking. So like when I go about building good copy, I'm trying to understand consumers pain points and how to approach them with them understanding that what we're providing is the solution without directly saying that, of course, right. I want to capture what they're thinking. And I think that specifically applies to like shorthand copywriting, you know, for PPC ads, Facebook, etc..

And so like, for example, right now everyone's losing their bags, right? Nobody wants to lose their bags, okay. So addressing that, you know, everyone's losing their bags and everyone's buying airtags to track their luggage, me included. Or if I'm writing like an op ed or a pitch, I always start with the headline or the subject line. It's like, what I want people to open with the feeling that I want them to get when they read what I'm writing.

Daniel Burstein: Yeah, don't bury the lead. That's a traditional journalist practice. I love that. Yeah, well, we talked about some lessons from the things you made in marketing. Let's look at some lessons from the people you collaborated with. So this first lesson is when things go wrong, it's an opportunity. And you learn this from a Elad Schaffer, the CEO of Faye. So how did you learn this from Elad?

Lauren Gumport: Yeah, so Elad is the CEO and co-founder of Faye Travel Insurance. He's my boss. He's an incredible boss who really like fosters me working remotely and understands that it inspires me.  I lost my phone in a water related incident and I wasn't available for 24 hours on my phone. And obviously, I just was terribly upset over it. I'm in communication. We're always available. Oh, my phone is my best friend. It's terrible. I mean, I'm, like, prying it away from myself at night so I can get some sleep. It's like a terrible habit. And. And so when I finally got , you know Apple, delivered me a new phone within literally 24 hours in the middle of nowhere. Arkansas, by the way, don't ask why I was in Arkansas, but it did happen. Apple really can reach you anywhere.

So and I apologized profusely. I mean, no emergency happened, right? It was everything was A-OK. And he said everything's fine. This is an opportunity. And he was right because the whole time I didn't have a phone and all these distractions, I sat and I created an entire plan to get Faye to a place in which we're a mission driven company.  I took my laptop, I sat out in nature, and I just kind of nailed it in that moment. I had just, I guess, a bunch of undisturbed thoughts because I didn't have my phone tied to me. And I appreciated that piece of advice. You know, he has great perspective and frankly he acts as half therapists, many times. Yeah he's the boss, but he's also really I swear, he's like my therapist. My CEO.

Daniel Burstein: That's a good CEO to act as a part time therapist too. I love that idea when things go wrong, it's an opportunity, right? There's always an opportunity in everything. Just if we look at it in the right way, right. Also that idea, I wonder, are you now like you're going to like purposely unplug at times or you know, I've seen I have not been good at this, but people who message like, okay, hey, for 4 hours this day or whatever, everything's turned off you won’t be able to reach me because like you said, you just maybe need to go out in nature and think and brainstorm and concept like, have you ever have you been yet able to work this into your workflow?

Lauren Gumport: You know, I don't think I'll ever be that person.

Daniel Burstein: I know I would want to be that person too.

Lauren Gumport: Yeah. And it's like there are, you know, when I take a vacation though, I take a vacation. So I will just say I take a vacation. But, you know, I will say that I am trying to be the person who doesn't sleep with a phone on the bedside table next to them. I'm trying to put my phone on the other side of the room, and that's actually working quite well because you're not waking up in the middle of the night and immediately checking your phone, which is kind of wakes up your brain, etc..

Daniel Burstein: So, all right. Let's look at the next lesson you said, don't spray and pray. And you learned this from Parry Headrick, Founder of Crackle PR. So how did you learn this from Parry?

Lauren Gumport: So if you're in PR, you should be following Parry Headrick. He is just he says everything that PR professionals are thinking. So I didn't necessarily learn this from him, but he put it into words that are it's exactly what it means. You cannot send a basic PR pitch, the same one to hundreds of reporters and expect them to be interested in your story.

You need to tailor your approach to specific reporters and what they write. For example, hey Vanessa, I saw you wrote about this topic. I wanted to introduce you to X product because we also address x scenario. Let me know if I can be a source for you for future stories my co-founder can talk to you about. And then you list three topics, right?

And Vanessa knows you read her articles, you reached out. You're not sending the same pitch to everybody. Parry has some very keeping it real type of PR tips. If you need a crash course in PR, I would follow him on LinkedIn. He’s hysterical. But this this approach has always helped me in PR to achieve top tier media for the brands that I work for.

Daniel Burstein: FIrst of all I love hearing this because at Marketing Sherpa, like is said, we get pitched all the time and we get, you know, some really good pitches. And there's also just a ton of spray and pray and they are so focused on themselves, right. But can you walk us through like specifically how you did this for, you know, like a mention you got. You know I was looking at your application, it was Wall Street Journal and USA Today, I think you mentioned New York Times, you gotten some really good mentions. Like for the Wall Street Journal ones where you researching that reporter first, like how specifically were you doing that?

Lauren Gumport: So I make a targeted media list of who's covered X topics. I reach out with timely data if it's like holiday planning, because Thanksgiving is coming up, for example. And there's a reporter that's writing about holiday travel. I'm sending a pitch to them. I remember when I was at Playbuzz, I noticed that this reporter was covering startups with like personal stories about their investors. So, I pitched them and I told them, hey, our lead investor loves our product, believes in us so much to the point where they even reserved an office just for themselves within our office so they could work in the same environment as us full time. And that got us the story.

You know, another way of this story was just understanding what was newsworthy. We had a funding round one time again at Playbuzz. Disney was one of the investors, not the lead investor, but one of the investors. And that's really big. It's really big news. So I led with that and it resulted in probably like I think it was like Bloomberg, Wall Street Journal, The Financial Times, all of the above. And more recently, you know, I ran into a New York Times reporter at a hotel opening party, found out she was from San Diego. And I messaged her personally because I'm from San Diego. So it's personal, long term relationships and just being relevant. Nobody wants a sales pitch.

Daniel Burstein: I always say people want to be served they don't want to be sold, right. You know, it’s true, and as a reporter on the other line, like we want case studies, we want the guests, that's something we need that we work hard for. So I don't want to ignore pitches. I don't want to say no to pitches. I want them. But you know, there are so many that are so relevant. Again, so many I get they are focused on themselves or whatever they're selling. There's so much corporate PR speak, like even when you're like, okay, we've got this good case study, you know, let's get some advice for the marketers, let’s get some advice for our audience, you know real advice from a real human being. It's so much like corporate PR speak with, well, let's work in the keywords and the product mentions. We need to get in because we're getting that mention versus talking like a human being.

Lauren Gumport: 90% of pitches are probably trash. I think they're trash. And, you know, my pitches are so it's like, yo,  saw you covered this. Would you be interested in this? I can speak to and I give them three topics super casual and I cannot remember the last time I spoke to reporter on the phone. It's all via email. They don't have time to speak on the phone.

Daniel Burstein: Yeah, exactly. Yeah. I mean, I get so many pitches, it's like here's a bit and like, oh, let's set up a call everyone wants to set up. They're like they're like sales reps. It's kind of like, no, I need the information now. The other thing I want to mention is, like how much of your time or do you have advice around there of how much you invest into PR? Because PR can be very time consuming.  When you said Parry I assume this was your PR agency and you had a PR agency working. So the fact that you're bootstrapping it, doing it yourself, and I'm sure there's many other things you're doing. So how do you balance that time investment that PR takes?

Lauren Gumport: So PR takes, you know you have to do a lot of writing and a lot creating new and thought provoking content. So you can't use the same thing over and over again. I would say we're a startup. I don't have budget for a PR firm yet. When I do, I will be talking to Parry. I think that probably 50% of my time is spent on PR, which is more than media relations, right. It's like speaking submissions for our executives at events, it's award submissions and at the end of the day, we're really focused on building this trust and credibility to be the most beloved, most trusted travel insurance company worldwide, eventually, currently in America. And that takes an incredible amount of time and commitment. And I would say to people who don't have in-house communications or an in-house PR pro and they're early stage and they're looking to get a PR firm, I wouldn't expect much. Because you can't give that PR firm so much of your time and they're not living and breathing your product. You need to, in my opinion, have somebody in-house working on comms if you're early stage to be truly successful with your narrative from the get go.

Daniel Burstein: And also since you're in-house, like how much are you able to shape your narrative?? So like a bigger company, it tends to be like it's just flowing down. These things are going on. Let's try to get press for them. But you know, you're there, you're sounds like working directly with the CEO. Are you able to affect the things they’ree doing in the product? Are you able to affect the things are doing on the website or partnerships or different things are doing..

Lauren Gumport: Yeah, I'm not just not PR, I'm product copy, website copy, blog copy, social copy and PR messaging.

Daniel Burstein: So have you been able to say, hey, this would be newsworthy if we added this topic. Or  have you, you know, as you mentioned with the, you know, disclaimer copy to talk us through that, have you done that well?

Lauren Gumport: So as long as things are compliant, we're okay, right? So, everything needs to be compliant, creative and fun, but compliant. S,o I will send a batch of content to be reviewed all at once. And then if it's been reviewed, I will not send the same piece of content ever to get reviewed again, right. So that saves quite a bit of time. I have a bank of content.

But you know, I think when it comes to PR, you know, content has to be compliant when it comes to your product and services and travel insurance. When it comes to PR, we're providing commentary about the industry and tips on holiday booking travel and third party data based on studies we're doing. So I don't need to check that that's compliant. I mean, that has everything to do with what we can comment on and how we position ourselves. But nothing to do with our products specifically. Say travel insurance is getting mentioned in those stories because of our executives getting quoted right. So, yeah, I hope that answers your question.

Daniel Burstein: Yeah. But are you, I assume, monitoring compliance there,  because when an executive speaking on behalf of the company, someone needs to be protecting the brand.

Lauren Gumport: Everything goes so every piece of copy goes through me, social blog, website, product, etc. and everything that you see on the website or in the product itself also goes through compliance. And it ads more time spent. I mean, it's not so quick to turn around copy like that that needs to be reviewed for compliance.

Daniel Burstein: Yeah, that's always a challenge. Let's look at one more lesson here. If you're not embarrassed about the first iteration of the product you put out, then you're doing it wrong. And that's from Dan Green, the Co-founder and CTO of Faye. So what can perfectionists learn from Dan?

Lauren Gumport: Wow. So you know, working at Faye, I got the pleasure of seeing a product that didn't exist get created. And then it was launched, right? And I think when you're about to launch a product for the first time, there are so many things that you wish it had that were on the original list that you had to put on the back burner because you need to get to the market ASAP, right? And we knew we had such a great product market fit. We knew how much everybody would love our product. And so some of those things had to be delayed a little bit, right.

And I remember Dan saying that in a meeting and I remember really taking that to heart. It doesn't always have to be perfect. I think that message applies to everything. And the first iteration of your product doesn't have to be perfect. And we will fix things and we will iterate and we will improve and we will be the best. But it is okay to release something that is not perfect yet. Now of course we're perfect. It's been a few months.

Daniel Burstein: And how do you then get to perfect? And what I mean is, you know, there's that idea of the minimum viable product. I prefer a minimum awesome product because, you know, sometimes you get one exposure to a customer. That first exposure, if it doesn't meet their needs or they're wrong or they don't think it's good enough, then they're gone.

So, I mean, it doesn’t have to be perfect, it has to be a certain level of good or you're going to, you know, lose that opportunity with them. So you mentioned A/B testing. So what are you doing to then like, okay, learn about, you know, get that customer feedback from the customer from your marketing, to understand like, okay, here's the next iteration, next iteration, here's how we need to improve. Because it’s one thing to not be perfect coming out of the gate, which I totally agree with, but then you better have some continuous improvement baked in right?

Lauren Gumport: Oh, for sure. So we're constantly A/B testing, you know, we're constantly doing it with, for example, like our key call to action, you know, should it be get covered, you know, which is a little bit more fun, you know, protect your trip or should it be kind of what everybody's used to, which is get a quote, check pricing. And we had what we wanted it to be and then we tested it and checked pricing really checked out. You know, it was what was converting the most.

We also looked at, I would say the purchase flow. So, we saw where people were dropping off and we had some inklings as to why that was happening. And one of them was, hey, maybe we shouldn't ask for customers full name first. Maybe they don't want to provide that first. They want to provide their trip details first, where they're going and the dates, name later, for example. And that also worked. But again, we tested it. We drove a specific amount of traffic there. We waited a bit. We looked at the numbers and then we optimized.

Daniel Burstein: That's a really interesting point because one thing I think about or I've written about too, is the momentum marketing. The idea is like, how do you get that ball rolling with the customer? And so if you're starting with the thing the customer is most excited about, in this case, the trip verses starting with the things that you want or need, like email address or even worse phone number where they're like, Oh, this is just a sales pitch. I love that lesson.

Lauren Gumport: Yeah, yeah, definitely.

Daniel Burstein: All right. Final question here. We've talked about all different things, about what it means to be a marketer. What are the key qualities of an effective marketer, in your opinion Lauren.

Lauren Gumport: Effective marketer, I would say you have to be an excellent writer. You have to be scrappy. You pivot fast without getting emotional about it. I mean, you could have an amazing plan one day and the next day the company has completely changed course. And you just you can't cry about it. You got to just pick up and move on.

And I would say you think and plan ahead. At a certain point as a marketer and a comms professional, you need to understand seasonality. You need to plan ahead. You need to plan, you know, a few months in advance to really nail your campaigns if you have the resources. Of course, that's what I would say.

Daniel Burstein: I like that. I like scrappy. I have you know asked a lot of people this question I haven't heard Scrappy before, but it's very true. You've got to be scrappy, especially in a startup. You got to just figure it out, right?

Lauren Gumport: Of course you have to be scrappy and it's like, you know, nowadays everyone's like, well, I just want to do one job, one specific role at the company. And it's like in startup life, it's like, no, I'm wearing 5 to 10 different hats a day and I can't just be writing email marketing copy that's not reality in startup land.

Daniel Burstein: In startup land, very true. Well, thank you for sharing your lessons from startup land Lauren. It was very interesting.

Lauren Gumport: Thanks for having me. It was really fun.

Daniel Burstein: And thanks everyone for listening. We hope you got some good lessons for your marketing campaigns and career.

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