Five Years of Building Scalable People-First Companies

Five years ago, I stepped away from an in-house operator role and into something new: a solo advisory practice dedicated to helping Series A–C startups build strong, people-first foundations from the start.

What began as a six-month experiment has become the most fulfilling chapter of my career. 

Over these five years, I’ve had the privilege of advising more than 40 venture-backed startups — helping founders and people leaders turn ambitious growth goals into sustainable, high-performing organizations.

From Scaling Unicorns to Advising Startups

Before founding Shelby Wolpa Consulting, I scaled the people function at four unicorn companies — Palantir, Instacart, One Medical, and InVision. Those experiences showed me firsthand the importance of investing in people systems early, before hypergrowth magnifies the cracks.

Since then, I’ve advised 40+ startups across SaaS, fintech, healthtech, e-commerce, and cybersecurity. The questions may differ, but the core challenges are strikingly consistent:

• How do we scale culture as quickly as headcount?

• How do we enable high-performing teams where people want to build their careers?

• How do we create scalable people processes and technology infrastructure that enables a frictionless employee experience?

Five Lessons from Scaling 40+ Startups

Partnering with a wide range of startups has revealed clear lessons about what it takes to grow with intention. Along the way, client stories have brought these lessons to life:

1. Foundations pay compounding returns.

Companies that wait to implement job leveling, performance systems, and compensation structures eventually face painful, expensive HR debt. At Amperon, we built a robust backbone that improved operational efficiency and strengthened their ability to attract and retain top global talent, fueling the company’s ambitious expansion plans. 

2. Culture must be operationalized.

Values alone don’t scale; they must be translated into rituals, behaviors, and decision-making frameworks. At Whimsical, we codified the unique async norms for their fully remote team, spanning across 12 countries. We introduced onboarding rituals to help new hires ramp quickly, designed practices for calm collaboration, and organized summits to make distributed work both productive and personal.

3. People strategy is business strategy.

When the people team is embedded in core business priorities, companies scale faster and smarter. At Veriff, aligning talent strategy with their aggressive international expansion plans meant designing a global entity and EOR strategy. These weren’t “HR projects”; they were growth levers that unlocked new markets and customers worldwide.

4. Leaders are culture multipliers.

Managers are the single biggest lever for maximizing engagement, retention, and performance.  At Sana, we defined their performance management philosophy, rolled out a year-round program for delivering continuous and actionable feedback, and trained managers on leading effective 1:1s. The result: managers became a trusted extension of leadership, reinforcing culture and driving results at scale.

5. Well-being drives performance.

Prioritizing mental health and employee care isn’t a “perk”; it’s a competitive advantage. At Chubbies, leadership elevated well-being to a strategic priority. Together, we designed a multi-faceted approach that included DEI Committee programming, “Mindspace Wednesdays”, quarterly “Quiet Weeks”, and career development budgets, fostering a culture where people could thrive. 

Across every engagement, the goal has been the same: to design people systems that scale alongside the business, enabling startups to scale faster, execute smarter, and build high-performing teams.

Growing Beyond Advisory Work

While hands-on HR advisory remains my core focus, over the last five years, I’ve intentionally expanded my practice to scale impact beyond individual companies.

The work has taken shape in a few ways:

• Codifying playbooks. Seven comprehensive playbooks now give operators and fellow consultants proven approaches to building people-first foundations without starting from scratch.

• Leading industry research. Two years of the Distributed Work Survey and Report have surfaced insights into how remote and hybrid teams are evolving, shaping the strategies of founders, operators, and investors.

• Building community. Hosting events and dinners, bringing together people leaders to learn, share, and collaborate.

• Amplifying lessons. From conference keynotes to founder summits to one-on-one mentorship, I’ve shared what I’ve learned to support the next generation of HR leaders.

• Writing consistently. With the launch of Hustle & Heart, my newsletter has become a way to reach thousands of founders and people leaders with insights on scaling culture and people systems.

  
  

The shift has allowed me to move from impacting a handful of companies at a time to equipping hundreds of teams with the tools, data, and resources to succeed - all in service of reimagining how people, culture, and community can work together. 

Looking Ahead

Each milestone has been possible because of the founders, people leaders, operators, and investors who’ve trusted me to build alongside their teams. To each of you: thank you.

The next five years will reward companies that invest in their people strategy with the same rigor they devote to product and go-to-market. My mission is to help them build the people operations foundations to get there.

👉 If your company is preparing for its next stage of growth and you want a seasoned partner to help build the people systems that accelerate growth, let’s connect: shelby.wolpa@gmail.com.