Culture Uncovered

Michael Martocci, founder and CEO of SwagUp, built a global branded-merchandise and logistics platform from age 21. He talks about scaling a people-first culture, hiring for curiosity and ownership, shifting to a distributed team, and protecting culture through rapid growth and acquisition. Short, fast-moving stories about hustle, referrals, and giving people real responsibility.

If “no surprise medical bills, ever” sounds like a dream perk, Stack Overflow might be your next favorite place to work.In this episode, Jena chats with Stack Overflow’s Chief People & Culture Officer, Debbie Shotwell, about building an inclusive, mission-driven, fully remote culture where experimentation is encouraged and growth is real. They dig into how a beloved public Q&A platform for developers evolved into a global business with enterprise products, ads, and AI partnerships, plus how Stack Overflow navigates change with radical transparency.What you’ll learn:Stack Overflow’s public Q&A platform for developers, Stack Exchange network, enterprise tools, ads, and AI data deals with Microsoft, Google, AWS.From 2008 garage startup to $200M business serving devs in 118 countries.Fully remote for 320 Stackers across engineering, product, sales, marketing, and people teams.Welcoming culture with buddies, ERGs, flexibility, and safe experimentation (no one’s an expert in AI).Internal mobility via marketplace, Stack Overflow Academy, and 12-18% promotion rates.Transparent leadership post-restructuring, with growth and selective hiring ahead.Stack Overflow highlights:Founded: 2008Team size: 320 employees worldwideOwnership: Acquired by Prosus in 2021; operates independentlyWork model: Fully remote, global teamCulture: Mission-driven, welcoming, flexible, inclusive, experimental, transparentUnique Perks & programs:100% company-paid health benefits (medical, dental, vision) + HRA covering all deductibles16 weeks paid parental leave for all; 4-week sabbaticals after 5/9 yearsMonthly Learn, Share, Grow Days + $2,500 annual development budgetNine ERGs, monthly AMAs, inclusion/engagement surveys with actionInternal “marketplace” for cross-team projects and boomerang opportunitiesTo learn more about The Stack Overflow:Careers Page (They're hiring!)Linkedin PageDebbie's Profile

Unlimited PTO sucks if you aren't REALLY allowed to take it. At this company, it's different.Raft is building the foundation for AI-driven autonomous operations, and Jena Dunay sits down with Kaitlyn Lavin, Manager of People and Culture, to pull back the curtain.They talk about the company’s journey from a small, scrappy team to 325+ employees, the culture that drives innovation, and how Rafters thrive in an environment built on transparency, ownership, and continuous growth.What you’ll learn:How Raft supports national security organizations with cutting-edge autonomous technologyWhat makes Raft’s culture unique and why employees love being “Rafters”Perks like flexible “Take As You Need” PTO and education budgets tailored to individual growthCareer frameworks and internal mobility that empower employees to shape their pathHow the company keeps its culture strong across multiple hubs and remote teamsRaft highlights:Founded: 2019 Team Size: 325+ RaftersHQ: Tysons, VirginiaWork Model: Hybrid/remote, with hubs across the USCulture: Curious, innovative, transparent, and people-firstPerks & programs:Personalized learning and development budgetsInternal mobility across roles and programsTri-weekly all-hands with live Q&AEngagement initiatives that connect employees across locationsTo learn more about Raft:Careers Page (They're hiring!)Linkedin PageKaitlyn's Profile

Yes, pensions still exist. And yes, you need to check out this company that still offers them!In this episode, Jena chats with Globe Life's Chief Talent Officer, Rebecca Zorn, about living the company’s mission to Make Tomorrow Better, empowering tenacious team players, and strategic hiring.What you'll learn:How Globe Life operates and evolves as a 125-year old companyThe service-oriented, collaborative, empowerment-driven culture that rewards tenacity and continuous improvementWhy internal mobility thrives - with Rebecca's sharing her own unconventional pathDetails on the pension (vests after 5 years for lifetime income at 65), plus 401(k) match and moreLeadership programs like Accelerate, Activate, Ignite (with SMU) and mentoringAll of the upcoming hiring initiatives!Globe Life highlights:Founded: 1900HQ: McKinney, TXTeam Size: ~4,000 employees + 16,500 independent agentsWork Model: Employees in 43 states; remote, hybrid, or on-site by roleCulture Values: Service-oriented, collaborative, empowerment-driven, accountable, integrity-focused, tenaciousUnique Perks & programs:Active pension plan 401(k) Employee life insuranceTraditional health benefitsSubsidized fitness memberships via WellHubLeadership development: Accelerate (new leaders), Activate (high-potentials), Ignite (senior leaders with Southern Methodist University courses)Skills-based internal mobility and emerging leader pipeline in developmentTo learn more about Globe Life:Careers Page (They're hiring!)LinkedIn PageRebecca's LinkedIn Profile

If your idea of a great job includes loud sales pods, laughter, C-suite connections, and a built-in winter break, you’ll want to hear this one.The Millennium Alliance designs intimate, five-star events where buyers and sellers actually sit down together behind closed doors. Jena chats with VP of HR, Victoria Albuquerque, about the company’s 12-year journey from three events to dozens each year, the “team sport” mindset that drives performance, and why they’re gearing up to double in size.What you’ll learn:What The Millennium Alliance actually does for buyers and sellers at their eventsHow the company grew from three events to 40–50 in the US and 10–12 in EuropeWhat it’s like to work on a loud, open sales floor with leaders “in the trenches”How early-career salespeople build real relationships with Fortune 500 executivesWhy internal mobility, hands-on coaching, and recognition are core to the cultureHow the team is preparing to double headcount in the next 12–18 monthsThe Millennium Alliance highlights:Founded: 2014 Team Size: <200 employees globallyHQ: New York CityWork Model: Primarily in-office with employees across the US and EuropeCulture: Supportive, fun, high-performing, “team sport environment,” ambitious and humanUnique Perks & programs:Heavy focus on sales and leadership training and developmentReal internal mobility: entry-level sales to running departments over timeDaily access to senior executives and decision makers as core to the roleCo-founders on the sales floor and leaders “in the work” with real-time coachingWeekly shoutouts, employee-of-the-month and year-end awardsTeam events, offsites, company outings, volunteer daysDedicated employee for culture and engagementWellness initiative: extra 20 minutes at lunch for the gym or personal timeCompany-wide shutdown over end-of-year holidays without using PTOTo learn more about The Millennium Alliance:Careers Page (They're hiring!)Linkedin PageVictoria's Profile

I'm obsessed with this company. Truly. Not just because of what they do - but how they operate.Meet Ashby, the all-in-one ATS with CRM, scheduling, surveys, analytics, and onboarding. In this episode, Jena Dunay talks with Jim Miller, VP of People and Talent, about their document-first async culture, "frustratingly patient" hiring, and randomized offsite dinners that accidentally became tradition.What you'll learn:How Ashby's async remote model uses documents over meetings and communication norms for Slack, email, and DocsThe power of "frustratingly patient" hiring focused on quality over speedRandomized offsite dinners and company trips that build real connectionsJim's exact pitch strategy that got him hired at Ashby after being their customerTransparent job descriptions that tell candidates why NOT to applyAshby Highlights:Founded: 2018Team Size: 250+ employees across 28 countriesHQ: San Francisco, CaliforniaWork Model: Fully asynchronously remoteCulture: Intentionally transparent, autonomous, impact-focusedUnique Perks & Programs:Company-wide offsites (Mexico trip with family option)Randomized dinners at offsitesProfessional development budgets for allInternal job alerts before public postingNo time-based hiring quotas, quality firstTo learn more about Ashby:Careers Page (They're hiring!)Linkedin PageJim's Profile

Running a restaurant can feel like a nonstop juggling act.But what if you had a digital partner taking the paperwork off your plate? Meet MarginEdge, the restaurant management platform bringing automation and real-time data to simplify back-of-house operations. In this episode, Jena Dunay talks with Roy Phillips, Co-Founder of MarginEdge, as they dig into the startup’s origin story, culture rooted in hospitality, and vision to make running a restaurant more enjoyable and efficient.What you’ll learn:How MarginEdge solves real restaurant challenges with software automationThe founding story born from firsthand experience in hospitalityBuilding a culture of transparency, ownership, and teamworkWhat Roy looks for in candidates : attitude matters mostGrowth goals and how they keep a connected remote-friendly team energizedMarginEdge highlights:Founded: 2015, after a chance meeting over coffeeTeam Size: 283 employees based across the U.S.HQ: Arlington, VirginiaWork Model: Remote-friendly with regular in-person gatheringsCulture: Hospitality-driven, transparent, and leadership-focusedPerks: Twice-weekly team lunches, lively office cafe, and company eventsTo learn more about MarginEdge:Careers Page (They're hiring!)Linkedin PageRoy's Profile

Yes, your company book club can have a Halloween plot twist and your PTO can include random “Take a Breath” days!Meet LifeSpeak, the wellness-first SaaS company where collaboration isn’t just talk and every remote employee really does have a voice, whether you’re dialing in from Toronto or Minnesota. In this episode, Jena sits down with Amanda Martel, Director of Human Resources, to dig into what it’s like working for a team that makes well-being and connection part of everyday work.What you’ll learn:How LifeSpeak evolved from mental health to a holistic digital wellness platform for organizations and individualsThe reality of building a collaborative, innovative culture in a remote setupPerks like flexible unlimited time off, well-being resources for employees, and company-wide unplug daysStructure, roles, where the team is growing, and what Amanda looks for in applicationsLifeSpeak highlights:Founded: Over 20 years agoTeam Size: About 130 employees in Canada and the USHQ: Toronto, hub in MinnesotaWork Model: Remote-firstCulture: Collaborative, innovative, and wellness-focusedPerks: LifeSpeak resources for employees, unlimited flexible time off, “Take a Breath” days, book club and sports chat channelsTo learn more about LifeSpeak:Careers Page (They're hiring!)Linkedin PageAmanda's Profile

Yes, you can buy life insurance without all the paperwork.Meet PolicyMe, Canada’s leading digital insurance platform that’s simplifying life, health, and critical illness coverage for families nationwide. In this episode, Jena chats with Vanesa Cotlar, VP of People and Culture, about what it’s like to work for a company that’s modernizing an entire industry while keeping its people curious, humble, and connected (even remotely).What you’ll learn:How PolicyMe is transforming insurance from paper-heavy to fully digitalWhy “humble high achievers” are the secret to their successHow curiosity fuels growth through AI, leadership training, and learning budgetsWhat flexible, remote-first work looks like when connection actually worksHow PolicyMe keeps culture strong while scaling fastWhat their REACH values mean in real life and how they shape hiringPolicyMe Highlights:Founded: 2018Team Size: 100+ employeesHQ: Toronto, Ontario Work Model: Remote-first with optional in-office Thursdays Culture: Curious, humble, high-achievingUnique Perks & Programs:Work-from-anywhere flexibilityTwice-yearly company events : think Toronto Island trips and circus troupes!Local hub meetups with budgets for regional gatheringsAI Guild for experimentation and cross-departmental learningLearning budgets for courses, books, and leadership trainingPopcorn tasting Fridays (yes, really!)To learn more about PolicyMe:Careers Page (They're hiring!)Linkedin PageVanesa's Profile

What do you get when smart AI-powered learning meets a remote-friendly, no-jerks work culture? Absorb Software: a rapidly growing team that’s all about learning, connecting, and keeping things real while scaling globally. In this episode, Jena catches up with Cheryl Yuran, Absorb’s CHRO, to chat about how they build connection across time zones, support career growth in a fast-paced environment, and why their AI-driven LMS makes life easier for both employees and HR pros. Whether you’re curious about remote culture or clever learning tech, this one’s worth a listen.What you’ll learn:How AI-powered learning enhances individualized development and eases administrative burdensThe role of a “no jerks” policy in fostering a respectful and productive workplaceStrategies for building strong connections in a distributed workforce, including unique social initiativesCreative career growth pathways designed to match diverse employee ambitionsInsider hiring tips, including Absorb’s candidate portal that helps job seekers stand outAbsorb LMS Highlights:Founded: 2003Team Size: Nearly 600 employees across six countriesWork Model: Remote-first, with optional office spacesCulture: Fast-growing, adaptable, and value-driven with a strong commitment to learningInitiatives: Active social groups, mentoring via an AI-backed platform, and personalized career laddersHiring Focus: Growth concentrated in customer-facing roles like sales and account managementTo learn more about Absorb LMS:Careers Page (They're hiring!)LinkedIn PageCheryl's Profile