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 technology
• What 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 growth
• Career frameworks and internal mobility that empower employees to shape their path
• How the company keeps its culture strong across multiple hubs and remote teams

Raft highlights:

Founded: 2019
Team Size: 325+ Rafters
HQ: Tysons, Virginia
Work Model: Hybrid/remote, with hubs across the US
Culture: Curious, innovative, transparent, and people-first

Perks & programs:

• Personalized learning and development budgets
• Internal mobility across roles and programs
• Tri-weekly all-hands with live Q&A
• Engagement initiatives that connect employees across locations

To learn more about Raft:

• Careers Page (They're hiring!)
• Linkedin Page
• Kaitlyn'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 company
• The service-oriented, collaborative, empowerment-driven culture that rewards tenacity and continuous improvement
• Why internal mobility thrives - with Rebecca's sharing her own unconventional path
• Details on the pension (vests after 5 years for lifetime income at 65), plus 401(k) match and more
• Leadership programs like Accelerate, Activate, Ignite (with SMU) and mentoring
• All of the upcoming hiring initiatives!

Globe Life highlights:

Founded: 1900

HQ: McKinney, TX

Team Size: ~4,000 employees + 16,500 independent agents

Work Model: Employees in 43 states; remote, hybrid, or on-site by role

Culture Values: Service-oriented, collaborative, empowerment-driven, accountable, integrity-focused, tenacious

Unique Perks & programs:

• Active pension plan
• 401(k)
• Employee life insurance
• Traditional health benefits
• Subsidized fitness memberships via WellHub
• Leadership development: Accelerate (new leaders), Activate (high-potentials), Ignite (senior leaders with Southern Methodist University courses)
• Skills-based internal mobility and emerging leader pipeline in development

To learn more about Globe Life:

Careers Page (They're hiring!)

LinkedIn Page

Rebecca'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 events
• How the company grew from three events to 40–50 in the US and 10–12 in Europe
• What 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 executives
• Why internal mobility, hands-on coaching, and recognition are core to the culture
• How the team is preparing to double headcount in the next 12–18 months

The Millennium Alliance highlights:

Founded: 2014
Team Size: <200 employees globally
HQ: New York City
Work Model: Primarily in-office with employees across the US and Europe
Culture: Supportive, fun, high-performing, “team sport environment,” ambitious and human

Unique Perks & programs:

• Heavy focus on sales and leadership training and development
• Real internal mobility: entry-level sales to running departments over time
• Daily access to senior executives and decision makers as core to the role
• Co-founders on the sales floor and leaders “in the work” with real-time coaching
• Weekly shoutouts, employee-of-the-month and year-end awards
• Team events, offsites, company outings, volunteer days
• Dedicated employee for culture and engagement
• Wellness initiative: extra 20 minutes at lunch for the gym or personal time
• Company-wide shutdown over end-of-year holidays without using PTO

To learn more about The Millennium Alliance:

• Careers Page (They're hiring!)
• Linkedin Page
• Victoria'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 Docs
• The power of "frustratingly patient" hiring focused on quality over speed
• Randomized offsite dinners and company trips that build real connections
• Jim's exact pitch strategy that got him hired at Ashby after being their customer
• Transparent job descriptions that tell candidates why NOT to apply

Ashby Highlights:

Founded: 2018
Team Size: 250+ employees across 28 countries
HQ: San Francisco, California
Work Model: Fully asynchronously remote
Culture: Intentionally transparent, autonomous, impact-focused
Unique Perks & Programs:

• Company-wide offsites (Mexico trip with family option)
• Randomized dinners at offsites
• Professional development budgets for all
• Internal job alerts before public posting
• No time-based hiring quotas, quality first

To learn more about Ashby:

• Careers Page (They're hiring!)
• Linkedin Page
• Jim'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 automation
• The founding story born from firsthand experience in hospitality
• Building a culture of transparency, ownership, and teamwork
• What Roy looks for in candidates : attitude matters most
• Growth goals and how they keep a connected remote-friendly team energized

MarginEdge highlights:

Founded: 2015, after a chance meeting over coffee
Team Size: 283 employees based across the U.S.
HQ: Arlington, Virginia
Work Model: Remote-friendly with regular in-person gatherings
Culture: Hospitality-driven, transparent, and leadership-focused
Perks: Twice-weekly team lunches, lively office cafe, and company events

To learn more about MarginEdge:

• Careers Page (They're hiring!)
• Linkedin Page
• Roy'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 individuals
• The reality of building a collaborative, innovative culture in a remote setup
• Perks like flexible unlimited time off, well-being resources for employees, and company-wide unplug days
• Structure, roles, where the team is growing, and what Amanda looks for in applications

LifeSpeak highlights:

Founded: Over 20 years ago
Team Size: About 130 employees in Canada and the US
HQ: Toronto, hub in Minnesota
Work Model: Remote-first
Culture: Collaborative, innovative, and wellness-focused
Perks: LifeSpeak resources for employees, unlimited flexible time off, “Take a Breath” days, book club and sports chat channels

To learn more about LifeSpeak:

• Careers Page (They're hiring!)
• Linkedin Page
• Amanda'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 digital
• Why “humble high achievers” are the secret to their success
• How curiosity fuels growth through AI, leadership training, and learning budgets
• What flexible, remote-first work looks like when connection actually works
• How PolicyMe keeps culture strong while scaling fast
• What their REACH values mean in real life and how they shape hiring

PolicyMe Highlights:

Founded: 2018
Team Size: 100+ employees
HQ: Toronto, Ontario
Work Model: Remote-first with optional in-office Thursdays
Culture: Curious, humble, high-achieving

Unique Perks & Programs:

• Work-from-anywhere flexibility
• Twice-yearly company events : think Toronto Island trips and circus troupes!
• Local hub meetups with budgets for regional gatherings
• AI Guild for experimentation and cross-departmental learning
• Learning budgets for courses, books, and leadership training
• Popcorn tasting Fridays (yes, really!)

To learn more about PolicyMe:

• Careers Page (They're hiring!)
• Linkedin Page
• Vanesa'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 burdens
• The role of a “no jerks” policy in fostering a respectful and productive workplace
• Strategies for building strong connections in a distributed workforce, including unique social initiatives
• Creative career growth pathways designed to match diverse employee ambitions
• Insider hiring tips, including Absorb’s candidate portal that helps job seekers stand out

Absorb LMS Highlights:

Founded: 2003
Team Size: Nearly 600 employees across six countries
Work Model: Remote-first, with optional office spaces
Culture: Fast-growing, adaptable, and value-driven with a strong commitment to learning
Initiatives: Active social groups, mentoring via an AI-backed platform, and personalized career ladders
Hiring Focus: Growth concentrated in customer-facing roles like sales and account management

To learn more about Absorb LMS:

• Careers Page (They're hiring!)
• LinkedIn Page
• Cheryl's Profile