The Road To: People, Leadership & Culture
- Stephanie Roulic
- 29 minutes ago
- 5 min read
Building a startup isn’t just about product, funding, or growth metrics: it’s about people.
As companies move from scrappy early teams to scaling organizations, the real challenges shift. Foundership becomes leadership. Culture must be intentional, not accidental. Hiring, performance, and team health become strategic priorities rather than operational afterthoughts.
This evolution is where many startups struggle and where the strongest companies differentiate themselves.
The Road To: People, Leadership & Culture brings together key conversations from Startup Boston Week focused on the human side of scaling: how leaders grow alongside their companies, how People Ops becomes a strategic driver of success, and how culture and team sustainability shape long-term outcomes.
Across these sessions, founders, operators, and People leaders share practical insights on transitioning from founder to executive leadership and building systems that support accountability and growth. Whether you’re leading a team of five or fifty, these conversations offer tactical guidance and honest lessons from those navigating growth in real time.
Table of Contents:
Making the Business Case for People Ops: How HR Leaders Can Secure Resources and Support
Performance Management in Startups: Crafting the Perfect Approach for Your Team
Preventing Burnout in Startups: Creating a Sustainable, High-Performing Team
AI in People Ops: How Startups Can Harness AI to Build and Support Sustainable Teams
Boss Mode: Leveling Up Your Leadership as You Scale
Scaling a company requires more than business growth, it demands personal evolution from its leaders. As teams expand and expectations shift, founders must transition from scrappy builders to confident executives who can inspire trust, implement structure, and lead with clarity.
This session explores how leadership must evolve as companies scale and what it takes to grow alongside your business.
You’ll learn how to:
Shift from founder to executive by developing leadership skills that scale
Navigate leadership transitions through real founder success (and failure) stories
Evolve team structures and management dynamics as headcount grows
Build systems and processes that support scalable leadership
Develop a leadership presence that inspires confidence among teams, boards, and investors
Speakers: Michael Kadish, Joe Alim, Julie Meyer, Theresa Tribble
Making the Business Case for People Ops: How HR Leaders Can Secure Resources and Support
People Ops leaders often struggle to secure resources because their work is viewed as support rather than strategy. Yet strong People practices fuel growth, reduce risk, and build long-term company value.
This session explores how to position People Ops as a strategic driver of business success and how to communicate its impact in ways founders and finance leaders understand.
You’ll learn how to:
Position People Ops as a strategic function, not a cost center
Use data and metrics to advocate for People Ops investment
Align People initiatives with business objectives to drive measurable impact
Communicate priorities in ways that resonate with leadership and finance teams
Measure and demonstrate ROI on People Ops investments
Clarify the distinction between HR and People Ops to strengthen employer brand and talent alignment
Speakers: Abbey Newmark, Mark Duffy, Jon Beck, Ann P. Walsh
Performance Management in Startups: Crafting the Perfect Approach for Your Team
Startups must balance structure with flexibility. Too little structure creates confusion; too much slows innovation. The right performance management approach evolves with your stage of growth.
This session explores how startups can design performance management systems that support accountability, growth, and culture, without unnecessary bureaucracy.
You’ll learn how to:
Determine when to introduce formal performance management
Evaluate continuous feedback vs. structured reviews
Deliver meaningful feedback in small, fast-moving teams
Align compensation and promotions with performance practices
Build a culture of feedback and accountability
Navigate the tension between coaching for growth and making difficult termination decisions
Speakers: Christina Luconi, Trupti Banda, Laura Poisson, Tania Philipp
Preventing Burnout in Startups: Creating a Sustainable, High-Performing Team
Startup speed and lean teams fuel innovation, but without intentional leadership, they can also lead to burnout. Sustainable performance requires systems, culture, and leadership practices that protect energy while maintaining momentum.
This session explores practical strategies for building resilient, high-performing teams without exhausting your people.
You’ll learn how to:
Recognize early warning signs of burnout and intervene proactively
Promote well-being while maintaining lean operations
Understand leadership’s role in fostering resilience and sustainable performance
Use flexible work policies and benefits to support team health
Maintain motivation and energy in resource-constrained environments
Speakers: Sandra Ma, Morgan Mosher, Alison Campbell, Allison MacLeod
AI in People Ops: How Startups Can Harness AI to Build and Support Sustainable Teams
AI is transforming the workplace - and People Ops is no exception. From hiring to engagement and retention, AI tools can streamline operations and unlock insights, but they also introduce ethical and operational considerations.
This session explores how startups can use AI to build efficient, human-centered People practices.
You’ll learn how to:
Improve hiring and talent acquisition using AI-driven tools
Evaluate and select AI solutions for People Ops functions
Navigate ethical considerations and bias risks in AI-driven HR processes
Leverage AI insights to enhance engagement and retention
Understand AI limitations and where human oversight remains essential
Speakers: Ryan Mahoney, Jen Paxton, Felicia Jadczak, Jason Lavender
Existence to Excellence: Using Culture to Scale with Soul
As startups grow, culture can either erode or become a powerful advantage. Building an intentional culture early helps companies scale with alignment, purpose, and resilience.
This session explores how to define, operationalize, and evolve culture so your company, customers, and team thrive together.
You’ll learn how to:
Define culture and understand its importance from day one
Establish cultural foundations in early-stage companies
Operationalize culture across the employee lifecycle
Maintain discipline while allowing culture to evolve
Scale culture intentionally as your company grows
Speaker: Christina Luconi
As startups grow, the challenges shift from building the product to building the organization that sustains it. Leadership must evolve. Teams need structure without losing agility. Culture requires intention. And People strategy becomes inseparable from business strategy.
The conversations in this Road To series reinforce a powerful truth: companies don’t scale, people do.
Founders must learn to lead at new altitudes. People Ops must move from support function to strategic partner. Performance and feedback systems must mature alongside the business. Teams need resilience, not burnout. AI can enhance the employee experience when implemented thoughtfully. And culture, when nurtured deliberately, becomes a company’s greatest competitive advantage.
None of these elements emerge by accident. They are built through intention, communication, and a willingness to grow as the company grows.
If there is one takeaway, it’s this: invest in your people and leadership practices as early and deliberately as you invest in product and growth.
