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