Episode #85: Meet the Startup Turning Employee Departures Into Brand-Building Opportunities

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• Where is the transcript for this webinar?

  Samantha Herrick:
  Welcome to the Tech Optimist, where innovation meets possibility. I’m Samantha Herrick, your host, here to guide you through the stories shaping tomorrow’s world. Every week we dive into bold ideas and extraordinary people who dare to reimagine what’s possible.

  Today, we’ll uncover a story that’s not just about technology, but about resilience, transformation, and purpose. This company helps you tackle the if and when. It’s a journey of disruption, ambition, and hope, and I promise it’ll leave you inspired. Let’s get started.

  Andrew Hamilton:
  We’re ultimately providing support at the end of the employee life cycle that has kind of been a forgotten landscape.

  Samantha Herrick:
  That is Andy Hamilton, co-founder and CEO of When.

  Andrew Hamilton:
  And our promise is that the last impressions are lasting impressions. So, we want to make sure that we treat people on the way out the same way we treat them on the way in.

  Mike Collins:
  There’s a dynamic economy, people are moving, and so…

  Samantha Herrick:
  Come on. I don’t have to tell you who that is. That’s Mike Collins, founder and CEO at Alumni Ventures.

  Mike Collins:
  It’s a little bit like death and taxes—I feel really good about When. There will always be a place in the market. One of the reasons I think we were excited to be an investor is this is a market that’s always going to exist.

  Samantha Herrick:
  And you know me, I think, at this point. My name is Samantha Herrick, your producer and host. My goal is to bring you closer to the visionaries shaping tomorrow’s world. As a storyteller, I thrive on uncovering the human side of technology. I’ve spent my time with this podcast connecting ideas with people, turning complex concepts into engaging stories. Whether it’s the latest startup revolutionizing industries or breakthroughs redefining how we live and work, I’m here to explore it all with and for you. So let’s dive into the future together.

  Welcome back to the Tech Optimist everyone, where we explore the bold ideas and brilliant minds shaping the future. I’m your host, as I mentioned earlier, Samantha Herrick, and today we’re stepping into a topic that often hides in the shadows of the employee life cycle: offboarding.

  Now, let’s face it—endings are hard, especially in the workplace. But what if there was a way to turn those transitions into seamless, even empowering experiences for everyone involved? That’s exactly what When, a Chicago-based startup, is making possible. Led by CEO Andy Hamilton and fresh off raising $4.6 million in seed funding, When specializes in managing the tricky terrain of employee offboarding.

  Their mission is simple yet profound: to ensure that benefits transition smoothly while leaving a positive legacy for departing employees and companies alike. Offboarding isn’t just a box to check—it’s a chance to protect your brand and nurture relationships. Today, we’re going to uncover how When is reshaping this often-overlooked process into a strategic advantage. Ready to rethink how endings could lead to new beginnings? Let’s dive in.

  Speaker 4:
  In today’s volatile job market, employee turnover is skyrocketing.

  Samantha Herrick:
  This is a quick sales video done by the When team.

  Speaker 4:
  And it’s costing companies more than just money. Layoffs and departures are tarnishing reputations, crushing morale, and overwhelming HR teams. For existing employees, the transition is daunting, especially when it comes to maintaining health coverage during this challenging time.

  At the core of this problem is COBRA, an outdated and inflexible system that fails to meet the needs of modern employees, leaving them with expensive, confusing, and inadequate options.

  But what if there was a better way—a way to support your employees through one of life’s most stressful transitions? Say hello to When: redefining offboarding, elevating the exit experience, and reducing COBRA expenses.

  When’s AI-powered platform and user-friendly interface provide personalized guidance, empowering employees to make informed decisions about their health insurance options.

  In addition to health insurance, When’s comprehensive platform offers a wide range of resources and information, including help with 401k rollovers, career guidance, financial assistance, and more.

  For HR teams, When is a valuable partner in the exit process. It streamlines the transition process, provides extensive support to existing employees, reduces costs and risks, and alleviates the administrative burden on HR professionals, allowing them to focus on core tasks and initiatives.

  Don’t let exits undermine your values. Be ready for when it matters most, and show your employees that you’re there for them every step of the way.

  When—because last impressions are lasting impressions. Learn more at forwhen.com.

  Samantha Herrick:
  First, we’ve got an ad and a disclaimer. Don’t go anywhere.

  Speaker 5:
  Exceptional value creation comes from solving hard things. Alumni Ventures’ Deep Tech Fund is a portfolio of 20 to 30 ventures run by exceptional teams who are tackling huge opportunities in AI, space, energy, transportation, cybersecurity, and more. These game-changing ventures have strong lead venture investors and practical approaches to creating shareholder value. If you are interested in investing in the future of Deep Tech, visit av.vc/deeptech to learn more.

  Samantha Herrick:
  As a reminder, the Tech Optimist podcast is for informational purposes only. It’s not personalized advice and it’s not an offer to buy or sell securities. For additional important details, please see the text description accompanying this episode.

  Mike Collins:
  Hi everybody, it’s Mike Collins. I’m the founder and CEO of Alumni Ventures. I’m here with one of our portfolio companies today and the founder, Andy Hamilton, of a company called When. Welcome to the show, Andy.

  Andrew Hamilton:
  Thanks for having me, Mike. Excited to be here.

  Mike Collins:
  All right, so let’s just hop right in. What’s the elevator pitch for When? What do you guys do? What are you all about?

  Andrew Hamilton:
  Yeah, so we’re pretty unique. We are an offboarding solution, and we partner with employers to help in the exit of employees, voluntary and involuntary. Our mission is really to help employees in that job transition, to make sure they have a soft landing. We’re ultimately providing support at the end of the employee life cycle, which has kind of been a forgotten landscape.

  For employees, we’re here to be that support, but we’re also providing a technology platform that makes it really easy for them to find health insurance alternatives to COBRA. We also partner with Morgan Stanley and other companies to help with everything from 401k rollovers, career development, outplacement, job search, and more.

  For employers, we’re here to protect their brand and reputation by making sure we take care of people as they’re exiting, providing best-in-class service when somebody is leaving. Our promise is that last impressions are lasting impressions—we want to make sure we treat people on the way out the same way we treat them on the way in.

  And in return, we’re going to move a lot of the risk that COBRA participants typically bring to an employer’s health insurance plan. We’ll shift it to the ACA as we help enable people to find their own affordable health insurance during a job transition.

  Mike Collins:
  No, and again, our audience is a lot of entrepreneurial folks. This is just the nature of the world—much more energy goes into recruiting, onboarding, and that honeymoon period. But there should be equal weight and equal attention on the other part of the journey. We all move on to other things at some point.

  I couldn’t agree with you more, Andy. Last impressions—from both parties’ standpoint—in what’s sometimes a planned, sometimes unplanned, but often stressful and uncomfortable situation, can be made a lot better with a little bit of work, technology, attention, and empathy.

  Andrew Hamilton:
  Absolutely, and it should be. This was born, for many entrepreneurs listening, out of personal experience. My fellow co-founder, Dan Wertheimer, and I both went through reductions in force.

  My last company was acquired by Expedia Group, and I worked there for a couple of years post-acquisition. Then COVID hit, and I ended up closing down my division during COVID. That’s where I experienced the void in solutions at the end of the employee life cycle. Everything we had during onboarding and open enrollment, and all the point solutions available, just kind of evaporated.

  Dan went through a similar experience as well. And these were large companies that really cared about their employees. Like you said at the beginning, there’s so much effort and innovation around those initial engagements—whether it’s recruiting solutions, onboarding, or open enrollment. Employers have been neglected when it comes to solutions to help them with offboarding. That’s what we aim to bring to the table—to help companies do it better.

  Mike Collins:
  So Andy, a relatively new company. Where are you in your life cycle and journey?

  Andrew Hamilton:
  Yeah, so we’re at an early stage. We started down this path around four and a half years ago, and at first, it was just an idea. My background is prop tech, not HR tech, so I had to learn the HR and benefits space.

  We got to work understanding the problems and pain points for employers and employees. We officially launched this year with our first paying clients. Started with client one in the first week of January, and today we have over 2,000 clients, ranging in size from a couple hundred employees to thousands of employees.

  I think by January we’re going to have close to 550,000 employees on our platform.

  Mike Collins:
  Wow.

  Andrew Hamilton:
  So we’ve had a great growth curve this year. It’s exciting because we know what we’re doing is really impactful to employees.

  Mike Collins:
  Just taking a couple of steps back—what are the headwinds and tailwinds behind a company like yours, given the environment in general?

  Andrew Hamilton:
  Yeah, so it’s interesting. Probably the biggest headwind we face is that there’s nobody else really doing what we’re doing. You’d think that’s a great tailwind, but it actually works conversely.

  We’re the only ones getting the message out there—we’re the only solution. As a startup, we don’t have the resources to be doing Super Bowl ads, so it takes time to educate companies. That’s our hardest headwind: going against the status quo and the lack of conversation around this. But I think we’re doing a good job chipping away at that.

  The tailwind for us is the unfortunate economy. Things aren’t changing—companies will continue to go through layoffs and restructuring. AI will continue to impact the types of jobs available or eliminated going forward.

  And with the younger generation, they don’t stay at jobs as long as I did or my parents did.

  Mike Collins:
  Sure.

  Andrew Hamilton:
  They’re not here for the long haul. Turnover rates have declined rapidly from generation to generation. I think for Gen Z, the average tenure is about 2.3 years.

  So, whether it’s voluntary or involuntary turnover, companies have to start thinking about that transition process. We’ve seen with the younger generation that they’re vocal—if it doesn’t go well, they’re recording that exit interview. They’re going to post about it on LinkedIn, Glassdoor, TikTok, or Instagram. We have to get it right.

  Mike Collins:
  Yeah, we’ve seen some examples of really just horrific handling of situations, for sure.

  Andrew Hamilton:
  Yeah.

  Mike Collins:
  And again, like you said, obviously there are recessions, industries go up, industries go down, there are RIFs, there are layoffs. But even in industries that are doing really well, there can be changes in who’s winning and who’s losing.

  Samantha Herrick:
  All right, now let’s dive into a topic that’s transforming workplaces everywhere: employee turnover. The numbers paint a very revealing picture.

  In 2023, the average annual turnover rate across the US and its industries was 41%, with voluntary departures accounting for a striking 70%. According to BuiltIn, over four million workers leave their jobs every month—roughly 2.5% of the workforce. Industries like leisure and hospitality topped the charts with a 79% turnover rate, while government jobs were the lowest at just 18%.

  Now, what’s driving these shifts? Gallup reports that highly engaged employees can reduce turnover by 18%. But for businesses failing to engage, the costs are steep. Replacing frontline workers can eat up 40% of their salary, while for leaders the price can skyrocket to 200%.

  Looking forward, Gallup also found that 51% of employees are already exploring new opportunities, signaling even more movement ahead. Small and mid-sized businesses feel the pinch harder, with turnover averaging 12% compared to 9.9% for larger enterprises, according to LinkedIn.

  Understanding these trends isn’t just about numbers—it’s about adapting to a future where employee offboarding and retention strategies matter more than ever. This is where When comes in and why we feel they’re such an important company to spotlight in their own episode on the Tech Optimist podcast. So stick around as we explore more innovative solutions with Andy and Mike.

  Mike Collins:
  In a real hot market, people are switching jobs for different reasons. There’s a dynamic economy, people are moving, and so it’s a little bit like death and taxes. I feel really good about When—there will always be a place in the market. One of the reasons I think we were excited to be an investor is this is a market that’s always going to exist.

  Andrew Hamilton:
  Correct. Yeah. It’s an inevitable part of the life cycle—there is always an ending to a job.

  Mike Collins:
  For sure. So, talk to me a little bit about if you had an ask of our community—probably hundreds of people who, through one of our funds, are now owners of When—as well as our community and other co-founders. How can we help?

  Andrew Hamilton:
  I love it. So, most importantly to us is just talking to more employers. For us, the ideal customer profile is someone that’s self-insured, typically with a thousand or more employees—but we certainly deal with smaller companies as well.

  We focus on employers who want to improve their offboarding process and understand the risks from COBRA participation. Opening doors to those clients and making introductions is something we’d welcome. We typically speak with HR leaders, whether it’s a CHRO or Director of Total Rewards. On the finance side, CFOs or Directors of Finance are also key contacts. And if there’s a risk team, they certainly understand the value we bring.

  We’re also looking for partners—this could be for our marketplace, where we want to provide employees with solutions they need during a job transition. Today, we have partners for job search, career development, and 401k rollovers, but there are many more opportunities. We can be pretty creative in how we present those solutions to employees.

  Finally, there’s a sales partnership. If any listeners have strong relationships or happen to be brokers, we’d love to partner with brokers to bring our solution to employers.

  Samantha Herrick:
  Think you could help out When or want to connect? Visit them at www.forwhen.com—that’s www.f-o-r-w-h-e-n.com—or connect with them on LinkedIn.

  Mike Collins:
  Great. Yeah, and we’ll make sure there’s information in the show notes and links to help people reach out to you. But you’re in this space, and again a lot of our listeners are entrepreneurs or executives. What are three or four key takeaways when you’re on the giving end of this situation? Any thoughts or advice for CEOs?

  Andrew Hamilton:
  Yeah, from an entrepreneurial standpoint, this is my third startup and I’ve been fortunate to have success with the prior two. And knock on wood, I hope with this one as well.

  I like to say when people ask, “What is the hardest part of getting things rolling?”—in my opinion, it’s really around the pitch deck. The pitch deck is key, not just for raising capital and getting investment, but because it helps you understand the story and formulate your go-to-market plan.

  It’s often overlooked. People stress out about it and don’t realize its true impact. But I’ve found it’s hard work—it takes time and a lot of iterations to get it right. When done well, it helps investors understand the story, but also internally, it helps you craft your elevator pitch and communicate your message in a way that resonates during sales conversations.

  Mike Collins:
  It comes down to storytelling, right? I think great entrepreneurs understand that it’s a sales job—not only to customers but also to employees, investors, and everyone involved. Being an entrepreneur is essentially a sales job where you spend half your time in the early years raising money and the other half building a business.

  Being able to tell your story and vision to all stakeholders is essential. Like you, Andy, I’ve found that writing is a really powerful way to think, clarify your thoughts, practice, iterate, and evolve.

  I remember in jobs and startups I’ve done, after every meeting I’d run to jot down notes—what I thought I did well in telling the story, generating enthusiasm, and where I could improve. It doesn’t come naturally to everyone.

  Andrew Hamilton:
  I agree.

  Mike Collins:
  You can definitely be in awe of someone like Steve Jobs—a natural storyteller with an ability to draw people in. But for 99% of entrepreneurs, even the ones who are very good at it, a lot of work went into becoming good at it.

  Andrew Hamilton:
  Agree 100%. I’m an introvert—it doesn’t come naturally or easily for me to get up and do a podcast, or speak in front of investors or potential clients. But like you said, writing is a great way to get comfortable.

  Whether it’s writing a pitch deck or just writing out a story in my notepad, it’s amazing how much confidence and comfort you gain. When you later present to a group, you feel more prepared and able to tell the story naturally.

  Samantha Herrick:
  Here’s a thought for you: What if the simple act of writing something down could transform the way you achieve your goals, manage your mind, and even ignite your creativity? The science behind this is staggering, so hang with me as we dive into this a little bit.

  Samantha Herrick:
  First, let’s talk numbers. Writing down your goals doesn’t just make you feel organized, it makes you 42% more likely to succeed. Only 1% of people take the time to do this, but those who do are up to 10 times more successful, according to a Harvard business study. It’s not magic, its psychology and a commitment to action embedded into the brain.

  Writing by hand, not just typing, improves memory retention and clarity. It’s like giving your brain a filing cabinet to prioritize what matters. Research even shows that writing helps reduce stress and anxiety, boosts self-esteem, and stimulates creative problem solving. It develops critical thinking and offers emotional benefits, plus it’s becoming an increasingly valuable skill in the job market, with a career growth potential of 16% annually.

  If you’ve ever needed a reason to start journaling or storytelling, there it is. And here’s my favorite part—it creates a visual representation of your mental process. It’s like taking the intangible and giving it shape, making it real. Whether you’re scribbling goals, brainstorming the next big idea, or simply unloading your thoughts, every word written is a step forward. So, what are you waiting for? Pick up that pen, grab a notebook, and start creating clarity, focus, and maybe even a little magic.

  Speaker 5:
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  Mike Collins:
  All right, just the last segment here. There are a couple of quick-hitter questions that we ask a lot of our founders. What do you think of remote work?

  Andrew Hamilton:
  I like it. It’s here to stay. I think there’s no way around it, especially for startups. I like the flexibility, I like the comfort. I’ve been an engineer, I’ve worked with engineering teams, and I know how they work. It’s absolutely preferred so they can work on their schedule when they work best.

  I do miss the team aspect. I miss having that centralized location where you can gather and be in front of a whiteboard, or have your Agile board up on the screen and talk through it. It’s missed—it’s not the same virtually. You have to make the effort to connect with people online. You probably do more meetings than you want, but you have to. It’s here to stay, and I’m okay with it.

  Mike Collins:
  Yeah, listen, if you have a very traditional in-office environment, I think you have to really work hard to ensure you’re giving people deep work time and alone time because you’re going to have a range of introverts, extroverts, individual contributors, and collaborators.

  We went from a world where you had to work hard to avoid meeting after meeting after meeting, to now, with more remote and hybrid setups, where you have to work really hard to build times when you can get together and build culture.

  Certain jobs are absolutely better for people to be around a whiteboard in the afternoon—that cannot be replicated. You cannot be a junior person and be mentored and develop good habits sitting alone in your apartment. So yeah, there’s no single right or wrong.

  Andrew Hamilton:
  Yeah.

  Mike Collins:
  How do you keep your investors up to date, Andy?

  Andrew Hamilton:
  It’s a good question. I use a tool called Visible, and I send quarterly updates. Sometimes I miss a quarter or I’m late by a month, but to me, transparency is key. I want to get those quarterly updates out.

  Obviously, I meet with my board and we have board observers on a more frequent basis. I make myself available and reach out to some of my investors directly with asks—help with connections—and just let them know where we’re at, good and bad.

  I have a few investors who are strong operators too, and we have side meetings with them regularly. I feel strongly that entrepreneurs need to be picky and bring in investors who can truly be partners, not just check writers.

  Mike Collins:
  Yeah, I think there’s definitely the board investor group and then the non-board investor group. You have to be picky in both.

  For board members, it’s like getting married—you want to be careful, with trial periods and dating if possible. With non-board member investors, I say think of your favorite aunt or uncle—they largely leave you alone, but if you need help, they’re there to be helpful.

  Andrew Hamilton:
  That’s great.

  Mike Collins:
  Do you have an unusual trick or habit or company routine to build culture that you’d share with other entrepreneurs?

  Andrew Hamilton:
  I don’t know if I have an unusual trick. I’ve been doing this a long time, building decks that we go through during all-hands company meetings. I try to keep it fun.

  For better or worse, we’ve always inserted silly images from Stepbrothers or other movies to get a laugh. I’ve found that I don’t want to be the one doing all the talking, and I don’t necessarily want just managers doing it either. I want others in the company to be responsible for presenting at different meetings to keep everyone engaged.

  I had never done this until we brought in a great HR person, Alex Seiler, who introduced icebreakers. It may seem silly or like something you do in typical HR gatherings, but it’s a huge help. It gets people more open and ready to sit through a presentation, and that’s helped a lot.

  Mike Collins:
  This doesn’t come naturally to me, and I think for a lot of entrepreneurs. We’re pretty intense—we think about our business constantly and put out fires.

  But if you can take a few minutes to laugh, tell a story, ask about someone’s family, and go around the room—it’s really important. It doesn’t come naturally to me at all—

  Andrew Hamilton:
  No.

  Mike Collins:
  —but it’s really, really important. If you can’t do it yourself because it’s just not in your wiring, try to find team members who are wired that way and give them the power to do it.

  Andrew Hamilton:
  Do what should be done.

  Mike Collins:
  We spend so much time doing what we do, and you have to laugh occasionally, hear a story, or it’s just not worth it.

  Andrew Hamilton:
  Absolutely.

  Mike Collins:
  How do you stay energized? How do you keep your energy level up with this marathon? Again, you’ve done this multiple times—how do you stay productive but energized and take care of yourself?

  Andrew Hamilton:
  It starts with what you’re doing. You have to believe in that mission from the very beginning. Building a company around something that impacted you personally is the best way to continue to power through because you’re going to go through crazy ups and downs. It is never a linear path of great success. Usually, any success you have is guaranteed to be followed by something miserable shortly thereafter.

  For me, it starts at the beginning—just doing something you believe in. And partly, like you said, it’s how you’re wired. I’m absolutely wildly competitive. I don’t like to lose. Whether it’s trying to get investors, making sales calls, or going after somebody from a recruiting standpoint, that motivates me and powers me on a daily basis. You need to find whatever fills up your cup—you have to find that to keep it going because it’s a slog.

  Mike Collins:
  If you were to do—and last question, Andy—if there was a one-hour Zoom session you were to do with eight other entrepreneurs, what subject would you want to cover?

  Andrew Hamilton:
  Great question. I think, similar to what I said earlier, pitch decks—understanding how to craft the story. I majored in marketing. I did end up being an engineer and a programmer, but maybe that goes back to my marketing roots of wanting to figure out how to formulate a story and then tell that story. That’s probably my sweet spot.

  There are others who are great with financial organization and architecting solutions, but for me, it’s helping with that story.

  Mike Collins:
  Yeah. And we can all learn from each other on those things for sure, too, right? Because everybody has had to do that, every founder has had to do that, and we’ve all learned things, good and bad, along the way about what works and what doesn’t.

  So, Andy, it’s been a pleasure. Congratulations on your progress to date.

  Andrew Hamilton:
  Thank you.

  Mike Collins:
  I look forward to catching up with you. I visit Chicago regularly and look forward to grabbing a beer with you sometime.

  Andrew Hamilton:
  Yeah, we’ll do a Cubs-Sox game for sure.

  Mike Collins:
  Oh, that’s super. Next summer—summer in Chicago is much better than the winter for sure.

  Andrew Hamilton:
  Tell me about it, it’s horrible.

  Mike Collins:
  Good. All right, Andy.

  Andrew Hamilton:
  All right. Thank you for having me.

  Mike Collins:
  Be well, all right.

  Andrew Hamilton:
  Bye.

  Samantha Herrick:
  Thanks again for tuning into the Tech Optimist. If you enjoyed this episode, we’d really appreciate it if you’d give us a rating on whichever podcast app you’re using and remember to subscribe to keep up with each episode. The Tech Optimist welcomes any questions, comments, or segment suggestions. Please email us at [email protected] with any of those, and be sure to visit our website at av.vc. As always, keep building.