Culture Uncovered

In this episode of Culture Uncovered, Jena Dunay sits down with Rachel Kohn, SVP of People Operations at Sendoso, to explore how a remote-first direct mail and gifting platform builds connection, trust, and joy across a team spread over 37 states and nine countries.

Rachel shares her unusual path to the company: she led the people team at a competitor that Sendoso acquired, and agreed to help with the integration for six months before deciding to stay. The conversation digs into what it takes to blend two cultures after an acquisition, and why Sendoso surveys employees quarterly to keep a real pulse on a team that can't read the room in a hallway.

The episode also covers how the people team responded to pulse-survey feedback that the joy was missing, including a company-wide "Camp Sendoso" with close to 90% participation, as well as Rachel's candid reflections on rebuilding trust after layoffs and on cross-functional collaboration that she grades a B-minus.

What You'll Learn

• How Rachel moved from leading a competitor's people team to leading Sendoso's after an acquisition
• Why Sendoso runs engagement surveys quarterly instead of once or twice a year in a remote-first company
• How "fun is a strategy" shows up in practice, from garden kits to Camp Sendoso
• Why rebuilding trust after layoffs can take 16 to 18 months, and what that looks like for the people left behind
• How the company approaches growth and professional development when headcount is stable
• What kind of person thrives in a remote environment where reaching out first is part of the job

Company Highlights

• Industry: Direct mail and gifting software and services
• Customer Base: Sales, marketing, and HR teams sending gifts and direct mail to customers, prospects, and employees
• Company Stage: Founded over ten years ago, about 250 employees (roughly 180 in the US), remote-first across 37 states and nine countries
• Culture: Hard-working, joy-seeking, and intentional about connection across a distributed team
• Focus Areas: Customer experience, go-to-market growth, AI-powered go-to-market engineering, and rebuilding cross-functional collaboration

Unique Perks & Programs

• Camp Sendoso: A summer all-company event where employees received camping kits, were sorted into cabins, and earned badges
• Gifted Days: 21 company-wide days of rest, including a quarterly day of rest and an extra-long summer weekend
• Lifestyle Spending Account: $100 a month (or local currency equivalent) for anything from gym memberships to internet to dog grooming
• Growth-Centered Performance Reviews: Review cycles built around skills, experiences, and career goals instead of evaluation
• Electives Learning Pilot: Live learning through an outside platform, grown from 10 participants to close to 30
• National Sending Day Swag Drop: A limited-edition employee swag drop each March

To learn more about Sendoso:

Careers Page
LinkedIn Page
Rachel's LinkedIn

In this episode of Culture Uncovered, Jena Dunay sits down with Erin McAuley, Chief People Officer at Springline Advisory, to explore what it's like to build culture at one of the fastest-growing accounting and advisory firms in the country, a "big small firm" formed through the acquisition of a dozen firms in just three years.

Erin shares how a coffee meeting with CEO Tim Brackney, arranged by a former Pinterest colleague, pulled her out of tech and into accounting to help build a firm while simultaneously acquiring and integrating others. The conversation dives into Springline's "Scale with Soul" philosophy, including a "culture discovery" process, described as match.com for firms and powered by the Barrett Values Survey, that tests values compatibility before any acquisition moves forward.

The episode also covers how Springline decides what to standardize (like benefits) and what to leave local (like firm-specific holidays and traditions), its LEAP program for future firm builders, and candid advice on who thrives in a fast-moving, build-it-together environment.

What You'll Learn

• How Springline grew to 12 firms and 1,000+ employees in three years while preserving local culture
• How the "culture discovery" process uses the Barrett Values Survey to match firms before acquisition
• What "Scale with Soul" means in practice, from shared benefits to firm-specific holidays
• Why the "big small firm" model appeals to accountants in a tight talent market
• How cross-firm collaboration, like the tiger team formed around new tax legislation, creates value no single firm could build alone
• What kind of person thrives at a firm that is still being built

Company Highlights

• Industry: Accounting and advisory services
• Customer Base: Mid-market companies, from roughly $50 million to $5 billion in size, across industries including health care, finance, and tech
• Company Stage: Founded in 2023, 1,000+ employees across 12 firms (soon 13) in the US and India, ranked among the fastest-growing accounting firms in the country
• Culture: Relationship-driven, builder-minded, and committed to "Scale with Soul"
• Focus Areas: Culture-first acquisitions, national capability building, internal mobility, and top talent development

Unique Perks & Programs

• LEAP Program: A 16-month top talent program for future firm builders, covering pricing, competitive advantage, and leading through change
• Firm-Specific Holidays: A shared set of core holidays plus four firm-specific days, such as April 16th for tax-heavy offices
• Internal Mobility Across Firms: Opportunities to move across offices or specialties, such as business litigation or real estate tax, without leaving Springline
• Communities of Practice: Go-to-market and pricing series that connect professionals across firms
• Centralized Talent Acquisition: A professional recruiting team that smaller local firms couldn't afford on their own
• Preserved Local Traditions: Acquired firms keep the events and programs that made their cultures strong, like team outings to Chiefs games

To learn more about Springline Advisory:

Careers Page
LinkedIn Page
Erin's LinkedIn

In this episode of Culture Uncovered, Jena Dunay sits down with Rebecca Kerr, former Director of People & Talent at Hike2, to explore what it's like to build culture at a fast-growing technology consulting firm named after its founders' love of the outdoors.

Rebecca shares how she was personally recruited by co-founder Amanda Wodzenski through a direct LinkedIn message when the company was just 20 people — an early signal of how intentional Hike2's leadership was about building people infrastructure well before most companies would think to. The conversation dives into what pulled her away from a stable role at a large global company into an unfamiliar industry, and how Hike2 built a curious, collaborative culture suited to consultants navigating client environments that aren't always their own.

The episode also covers Hike2's standout National Parks pass perk, its "Trail Talks" lunch-and-learn program, and candid reflections on the communication growing pains that come with scaling quickly — plus why teachers, surprisingly, tend to make excellent consultants.

What You'll Learn

• How Hike2's founders prioritized building people infrastructure at just 20 employees, earlier than most companies do
• Why running toward a new challenge, not just away from a stable job, made the move to Hike2 the right call
• How Hike2 supports consultants who move between client cultures and their own internal one
• Why the company screens for comfort with ambiguity and real-time problem-solving over rehearsed interview answers
• What makes teachers surprisingly well-suited for consulting careers
• How Hike2 has had to relearn and improve internal communication as the company scales quickly

Company Highlights

• Industry: Technology and AI consulting
• Customer Base: Enterprise clients across multiple industries, served both remotely and on-site depending on client preference
• Company Stage: ~80 employees, grown from a 20-person team over four and a half years, remote-first
• Culture: High-performing, collaborative, and built around curiosity and comfort with ambiguity
• Focus Areas: AI and data capability building, leadership development, and scaling communication practices

Unique Perks & Programs

• National Parks Pass: A company-provided perk reflecting the team's outdoorsy culture and the company's own name
• Flexible PTO: Remote-first flexibility intended to help consultants recharge between demanding client engagements
• Accessible Leadership: An open-door culture where any employee can speak directly with leadership, even as the company has scaled to 80 people
• Trail Talks: Employee-led lunch-and-learns covering everything from technical skills to personal passions
• Exposure to Cutting-Edge Client Work: Broad, resume-building experience across industries and emerging AI technology
• Growing Leadership Development Investment: Increased focus on training and supporting people managers as the team has grown

To learn more about Hike2:

Careers Page
LinkedIn Page
Rebecca's LinkedIn

In this episode of Culture Uncovered, Jena Dunay sits down with Dale Klasko, SVP of People at Formation Bio, to explore what it's like to build culture at an AI-native pharma company reimagining the drug development life cycle from clinical trials through FDA approval.

Dale shares how she joined the company (then called Trial Spark) in March 2020 as part of its first fully remote cohort, and the early, tangible moment that cemented her belief in the mission: running a COVID-19 clinical trial within her first few months. The conversation dives into how she found the role through an often-overlooked strategy — building relationships with VC talent partners to get warm introductions into companies aligned with her interests — and how Formation Bio's four core values, including the standout "be a scientist," have stayed consistent through years of significant company growth and change.

The episode also covers Formation Bio's deliberate, hands-on approach to AI upskilling — including a company-wide "Citizen Builder Boot Camp" where employees shipped real internal tools in under three days — alongside its strong working-parent benefits and a candid reflection on the challenge of keeping expectations clear as AI capabilities evolve so quickly.

What You'll Learn

• How Formation Bio's mission to speed up drug development led it to acquire and own its own clinical-stage drug assets
• How to use VC talent partner networks as a job-search strategy to get warm introductions to startups
• What Formation Bio's four core values are, including the distinctive "be a scientist" approach to problem-solving
• How the company's Citizen Builder Boot Camp got non-technical employees building real AI-powered tools in days, not months
• What real examples of employee-built AI tools look like, from a custom skills-training app to an interactive onboarding assistant
• Why being explicit about fast-changing AI expectations is critical as the technology accelerates

Company Highlights

• Industry: AI-native pharmaceutical and drug development
• Customer Base: Patients awaiting new treatments, served through an end-to-end, AI-powered drug development pipeline
• Company Stage: 10-year-old company (formerly Trial Spark), Series D-funded (led by a16z in 2024), ~150 employees, headquartered in NYC with a new Boston office opening
• Culture: Mission-driven, first-principles thinking, and intentionally lean in structure
• Focus Areas: AI upskilling and tooling, R&D team-building under new leadership, and working-parent support

Unique Perks & Programs

• Generous Parental Leave: 18–20 weeks for birthing parents and 12 weeks for non-birthing parents, with strong cultural support for actually taking full leave
• Parents Employee Resource Group: A community built by employees (including Dale) offering events, a take-your-kid-to-work day, and ongoing connection for working parents
• Unlimited PTO: Flexible time off, particularly valued by parents managing unpredictable schedules
• Citizen Builder Boot Camp: A 2.5-day, company-wide AI building intensive where every participant shipped a working tool tied to their job
• Ask Enterprise AI Slack Channel: An always-on peer support channel where non-technical employees get real-time help solving technical AI problems
• Enterprise AI Tool Access: Company-wide subscriptions to tools like ChatGPT and Claude, paired with structured training and engineer "buddy" support

To learn more about Formation Bio:

Careers Page
LinkedIn Page
Dale's LinkedIn

In this episode of Culture Uncovered, Jena Dunay sits down with Matthew Brunwasser, Head of People Ops at Coverdash, to explore what it's like to build culture at a fast-growing, tech-forward commercial insurance company serving small businesses and contractors.

Matthew shares his unconventional path into people ops — from 13+ years running restaurants and poke bars in New York City, to agency recruiting post-COVID, to head-of-people roles at Bbot (acquired by DoorDash) and Sauce — and how a direct LinkedIn message from Coverdash's CEO led him to an industry he wasn't initially passionate about, but a team he immediately connected with. The conversation dives into how Coverdash maintains an "evolving collaboration" culture across a truly distributed workforce spanning the US, Serbia, and soon Latin America, including a core overlap window for real-time communication and heavy use of Loom videos to bridge time zones asynchronously.

The episode also covers Coverdash's benefits philosophy — built directly from employee engagement survey requests rather than guesswork — its responsible PTO policy that rewards results over face time, and an honest reflection on the challenge of building genuine personal connection across a workforce that tripled in just over a year.

What You'll Learn

• How Coverdash uses technology to modernize commercial insurance for small businesses and contractors
• How a distributed team across the US, Serbia, and soon Latin America stays collaborative despite major time zone gaps
• Why Coverdash relies heavily on Loom videos instead of long Slack threads or waiting for same-time availability
• How the company's "responsible PTO" policy ties flexibility to performance rather than time logged
• Why Coverdash builds new benefits directly from engagement survey requests instead of guessing what employees want
• An honest look at the challenge of fostering real personal connection across a workforce that tripled in just over a year

Company Highlights

• Industry: Tech-driven commercial insurance (insurtech) for small businesses, contractors, and consultants
• Customer Base: Small businesses and independent contractors historically underserved by traditional insurance carriers
• Company Stage: 4-year-old, Series A-funded company; ~95 employees (doubled in under a year), nearing profitability
• Culture: Evolving, collaborative, and intentionally built around flexibility and trust over rigid structure
• Focus Areas: Sales and operations growth, internal tech upskilling, leadership development, and cross-timezone connection

Unique Perks & Programs

• Responsible/Flexible PTO: Performance-based time off with no cap, exemplified by a top performer who took six weeks off in a year
• Survey-Driven Benefits Rollout: New benefits (like a recently added 401(k) and match) launched directly in response to employee survey requests
• Manager Book Club: A quarterly leadership development program (recent reads include Radical Candor and Who) paired with accountability check-ins
• Internal Tech Demo Days: Regular sessions teaching non-technical employees to build and use internal tools without relying on engineering
• Strong Internal Promotion Track: Nearly all current leaders, including the lead software engineer and sales/ops team leads, were promoted from within
• Expensed Team Bonding Trips: Spontaneous, leader-initiated outings (like a golf trip for the Rochester team) without requiring prior budget approval

To learn more about Coverdash:

Careers Page (they're hiring!)
LinkedIn Page
Matthew's LinkedIn
Small Businesses looking to confirm they have the best rates and policies possible

In this episode of Culture Uncovered, Jena Dunay sits down with Kaitlyn Borea, VP of HR and Talent at Vivrelle, to explore what it's like to build culture at a members-only luxury handbag and jewelry rental club founded by a husband-and-wife team.

Kaitlyn shares how a confidential executive search led her to Vivrelle, and what sealed the decision: leadership's genuine understanding of parenthood and work-life boundaries. The conversation dives into the unique challenge of leading HR for two very different employee populations under one roof — a traditional 9:30-to-6 logistics and operations team that hand-packs every luxury item, and a more flexible, Slack-driven corporate team — and how that shaped Vivrelle's deliberate return to an in-office culture.

The episode also covers Vivrelle's standout "bucket of remote days" perk, which gives corporate employees full autonomy over when to use flexible work time, along with candid advice for job seekers on identifying their non-negotiables by season of life, and why Kaitlyn believes small, scrappy startups offer unmatched growth exposure early in a career.

What You'll Learn

• How Vivrelle's founders got the idea for a luxury handbag rental service during their own wedding planning
• Why Vivrelle intentionally returned to a five-day, in-office culture rather than staying remote
• How the company's "bucket of remote days" gives corporate employees full autonomy over flexible work time
• Why leading HR for two distinct employee populations (logistics/ops vs. corporate) requires different approaches to benefits and culture
• How to evaluate a job opportunity by identifying your non-negotiables for your current "season of life"
• Why Kaitlyn believes small startups offer faster, higher-exposure growth than larger established companies

Company Highlights

• Industry: Luxury fashion rental / membership subscription service (handbags and jewelry)
• Customer Base: Members ranging from space-conscious city dwellers to frequent event-goers seeking variety without ownership
• Company Stage: Founded in September 2018, Series C-funded, ~70 employees, in-office five days a week in Manhattan
• Culture: High-trust, high-autonomy, casual, and intentionally low-stress despite operating in the luxury space
• Focus Areas: Logistics and operations excellence, growth marketing (newly built out), and sustainable (not aggressive) hiring

Unique Perks & Programs

• Bucket of Remote Days: 30 flexible remote days per year for corporate employees to use however and whenever suits their life
• Employee Membership Discount: Significant discount on Vivrelle's own luxury handbag and jewelry membership
• Extra PTO for In-Office Roles: Additional paid time off specifically for employees whose roles require daily in-office presence
• Opt-In Lifestyle Perks: Peloton, Citi Bike, and Kind Body memberships available based on individual interest
• Paid Birthday Off: A company-wide day off for every employee's birthday
• Access to Brand Events: Employee participation in pop-ups and partnership events (e.g., a Hamptons pop-up and a Kith collaboration celebration)

To learn more about Vivrelle:

Careers Page (they're hiring!)
LinkedIn Page
Kaitlyn's LinkedIn

In this episode of Culture Uncovered, Jena Dunay sits down with Kiley Ewing, Chief People Officer at McGuire Sponsel, to explore what it's like to build culture at a specialty tax firm that helps businesses save money through partnerships with CPA firms across the country.

Kiley shares her unconventional path to the role — joining as an external sales coach for five years before being asked to build out the company's HR function from scratch as Chief People Officer. The conversation dives into how she's spent her first year and a half laying real infrastructure: a new applicant tracking system, a PEO transition that improved benefits, a learning management system in progress, and a relaunched mentorship program.

The episode also covers the redesigned two-year Leadership Academy, built around coaching application over one-time training, and how McGuire Sponsel's GREAT core values (growth mindset, relationships, excellence, awareness, tenacity) show up in hiring, performance reviews, and day-to-day culture — including a hiring strategy built around training new grads rather than requiring tax experience.

What You'll Learn

• How McGuire Sponsel's CPA partnership model drives growth without going directly to businesses
• How Kiley's five years as an external sales coach led to her becoming Chief People Officer
• Why the Leadership Academy expanded from one year to two, shifting from training to coaching-based application
• How the GREAT core values (growth mindset, relationships, excellence, awareness, tenacity) are built into hiring and performance reviews
• Why McGuire Sponsel intentionally hires new grads without tax experience and trains them from scratch
• How employee-driven AI automation projects are reshaping efficiency across the firm

Company Highlights

• Industry: Specialty tax consulting (R&D credits, cost segregation, property tax, international tax, site selection)
• Customer Base: Businesses referred through a network of 500+ partnered CPA firms across all 50 states
• Company Stage: Founded in 2007, ~125 employees, headquartered in Indianapolis with offices in Detroit, Atlanta, Dallas, and Phoenix
• Culture: Relationship-driven, growth-oriented, and primarily in-office to support internal connection
• Focus Areas: Leadership development, structured onboarding/training for new grads, operational efficiency, and AI-driven process improvement

Unique Perks & Programs

• Summer Fridays: A post-tax-season flexibility perk allowing remote, as-needed availability on Fridays through the summer
• Two-Track Leadership Academy: A two-year, nomination-based program split into Emerging Leaders and Advanced Leader tracks
• Fully Paid Core Benefits: Health, dental, vision, life insurance, and short/long-term disability fully covered by the firm
• Generous PTO Scaling: Four weeks of PTO for all employees, increasing to five weeks after five years of tenure
• Pet Wellness Coverage: Supplemental insurance offerings beyond standard health benefits
• Annual Mentorship Program: A refreshed, year-round mentorship initiative for new hires

To learn more about McGuire Sponsel:

Careers Page (they're hiring!)
LinkedIn Page
Kiley's LinkedIn

In this episode of Culture Uncovered, Jena Dunay sits down with Kim Marsh, Former Global Head of Talent Acquisition at Pebl (formerly Velocity Global), to explore what it's like to build culture at a global employer of record company helping businesses hire talent in over 185 countries.

Kim shares how her move to Pebl was her third time working alongside her trusted CHRO, and what made the interview process itself feel different — real transparency from the team about what they were building and why the role was open. The conversation dives into how global hiring naturally builds humanity into company culture, since supporting employees across different countries, labor laws, and customs forces a more thoughtful, people-first approach than a one-size-fits-all policy ever could.

The episode also covers Pebl's "fail fast" ethos coming directly from leadership, its AI hackathons that have led to real cross-functional career moves, and candid advice for job seekers on bringing their authentic selves rather than trying to guess what an interviewer wants to hear.

What You'll Learn

• How an employer of record (EOR) removes the complexity of hiring talent across 185+ countries
• Why Kim treats interviewing like matchmaking, looking for authenticity and real two-way connection
• How Pebl's "fail fast" culture shapes how the team approaches new ideas, especially around AI
• How global hiring naturally builds more thoughtful, human-centered benefits and policies
• How Pebl's AI hackathons have led to real cross-functional career moves within the company
• Why job seekers shouldn't disqualify themselves from applying to a role that's a close fit

Company Highlights

• Industry: Global employer of record (EOR) and HR technology
• Customer Base: Companies hiring international talent without in-house expertise in global labor law and compliance
• Company Stage: Founded in 2012 as Velocity Global, recently rebranded to Pebl; 500+ employees, remote-first with hubs in Palo Alto and Toronto
• Culture: Ambitious, transparent, collaborative, and comfortable with rapid pivots
• Focus Areas: Global hiring complexity, AI-driven product evolution, internal mobility, and authentic candidate experience

Unique Perks & Programs

• AI Hackathons: Company-wide events where employees build and showcase tools, often sparking new cross-functional career paths
• Global Holiday Celebrations: Recognition of culturally diverse holidays (World Cup, Lunar New Year, Cinco de Mayo) reflecting the company's global workforce
• "Wow Wednesdays": Regular company gatherings where employees publicly recognize cross-functional colleagues for their contributions
• Flexible, Remote-First Structure: Primarily remote work with hybrid hub options and in-person leadership and team gatherings
• Localized Benefits by Country: Benefits and support tailored to each employee's local labor laws, culture, and life circumstances
• Strong Internal Mobility: Demonstrated pattern of employees moving across departments (e.g., RevOps to product, solutions engineering to sales)

To learn more about Pebl:

Careers Page (they're hiring!)
LinkedIn Page
Kim's LinkedIn

In this episode of Culture Uncovered, Jena Dunay sits down with Douglas Freeman, Chief Revenue Officer at Crunchr — and Jena's former boss — to explore what it's like to build a revenue team and company culture at a people analytics platform helping HR leaders turn workforce data into real business decisions.

Doug shares how a casual 30-minute conversation about revenue strategy led him to Crunchr, and what drew him to the opportunity after years working in HR tech and recognizing the exact problem Crunchr was built to solve. The conversation dives into Crunchr's three core company behaviors — think big, ship small, win together — and the three pillars Doug uses to build his own revenue subculture: discipline, distinctiveness, and desire, including why he deliberately hires people to be themselves rather than conform to a single sales persona.

The episode also covers real examples of how Crunchr helps organizations connect disjointed HR data — from predicting retirement waves to diagnosing regrettable turnover — and candid career advice on networking, staying in touch over the long term, and how to actually sell yourself in an interview.

What You'll Learn

• How Crunchr helps organizations unify fragmented HR data into a single source of truth
• What Crunchr's three company behaviors — think big, ship small, win together — mean in practice
• How Doug's three-pillar framework (discipline, distinctiveness, desire) shapes his approach to building a sales team
• Why Doug believes salespeople should be coached within their own personality, not molded into a single mold
• How to use "proof points" and concrete stories to stand out in an interview
• Practical advice for keeping a professional network alive over years, not just when you need something

Company Highlights

• Industry: People analytics / HR technology
• Customer Base: HR and business leaders at organizations ranging from 1,000 to 75,000+ employees, including multinational companies managing data across dozens of countries
• Company Stage: Founded in 2014 in Amsterdam, ~60 employees, with a second office in Boston
• Culture: Curious, accountable, and collaborative across a hybrid, multinational team
• Focus Areas: People analytics maturity, data trust and security, turnover diagnostics, and HR's growing strategic role

Key Practices & Frameworks

• Think Big, Ship Small, Win Together: Crunchr's company-wide behavioral framework for balancing ambition with iterative execution
• Discipline, Distinctiveness, Desire: Doug's subculture framework for building his revenue team, emphasizing consistency, individuality, and personal growth
• "Jenify It" Mentality: Encouraging team members to personalize processes within a shared structure, then share results — successes and failures — with the team
• Proof-Point Interviewing: Coaching candidates to bring concrete stories and results rather than vague claims of skill
• Build vs. Buy Guidance: Perspective on why maintaining sensitive people-data infrastructure internally is often harder than the initial build
• Long-Term Network Maintenance: A practice of making regular low-stakes introductions and personal check-ins to keep professional relationships genuinely alive over time

To learn more about Crunchr:

Careers Page (they're hiring!)
LinkedIn Page
Doug's LinkedIn

In this episode of Culture Uncovered, Jena Dunay sits down with Reuben Doetsch, Co-Founder and President of AvantStay, to explore what it's like to build culture at a fast-moving, remote-first hospitality company bringing hotel-level consistency to short-term rentals.

Reuben shares how frustration with inconsistent short-term rental experiences, combined with his background running a co-living company, led him and his co-founder to build AvantStay into a portfolio of over 3,500 properties across 60 markets. The conversation dives into the company's deliberately flat, global-first hiring philosophy — paying top talent well regardless of location, with no artificial leveling ceilings between onshore and offshore employees — and how that shapes a genuinely unified (not siloed) remote culture.

The episode also covers AvantStay's blunt, performance-driven approach to culture, including cutting formal culture programming in favor of real interpersonal connection, a mandate for employees to actively upskill in AI, and an honest acknowledgment that the company's fast-changing, low-structure environment isn't the right fit for everyone — and that's by design.

What You'll Learn

• How AvantStay's "hotel in the home" concept was born out of real frustration with inconsistent short-term rentals
• Why the company deliberately avoids different leveling criteria for offshore versus onshore employees
• How AvantStay builds genuine connection with a globally distributed team through regular in-person gatherings
• Why the company cut formal culture programs in favor of real manager relationships and shared work
• How AvantStay's new "Market Enablement Team" was created to solve lagging regional issues with fresh eyes
• Why Reuben openly says AvantStay isn't the right fit for everyone, and how that's addressed from the first interview

Company Highlights

• Industry: Tech-enabled hospitality (short-term rentals and boutique hotels)
• Customer Base: Travelers seeking unique, high-quality alternative accommodations, from large group homes to boutique hotels
• Company Stage: 8-year-old company, ~400-450 employees (down from a peak of 800), fully remote with ~200 field-based roles
• Culture: Performance-driven, transparent, fast-moving, and intentionally not for everyone
• Focus Areas: AI upskilling, global talent equity, acquisition integration, and operational agility

Unique Perks & Programs

• Vacation-Style Stay Credits: Employees can stay at AvantStay properties in other markets to build firsthand understanding of the business
• No Offshore/Onshore Ceiling: Equal advancement opportunity regardless of location, including senior leadership roles held by fully remote team members
• Flexible, Outcome-Based Schedules: Employees can structure their work around their life and location as long as outcomes are met
• Quarterly In-Person Gatherings: Regular team meetups plus natural gatherings around market and hotel launches
• High-Trust, Low-Micromanagement Culture: Trust is earned but extended broadly once established, including around scheduling and location
• Mandatory AI Upskilling: A company-wide expectation that employees actively learn and apply AI tools to remain competitive

To learn more about AvantStay:

Careers Page (they're hiring!)
LinkedIn Page
Reuben's LinkedIn