People Ops
Ready to connect with your peers in people ops and HR? Grab your free ticket for Startup Boston Week on Sept 14 - 18 today!
Managing Performance Without Avoiding the Hard Stuff: Feedback, PIPs, and Letting People Go
Every startup leader eventually runs into the same uncomfortable reality: someone on the team is no longer the right fit. Maybe expectations were unclear, the role evolved too quickly, performance never improved, or the company simply outgrew what was needed early on.
Whatever the reason, managing performance - and sometimes letting people go - is one of the hardest and most emotionally complicated parts of leadership, especially in fast-moving startups where teams are small and relationships are close.
You will walk away learning:
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What early signs may indicate someone is struggling in their role
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What effective, direct feedback actually sounds like in practice
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How managers can create clarity before performance issues escalate
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When performance improvement plans (PIPs) are useful and when they are not
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How to determine whether to continue investing in someone versus moving on
Most managers are never formally taught how to handle performance issues well, they learn through uncomfortable trial and error.
Whether you are managing your first team or leading a growing organization, this session is designed to help leaders navigate difficult people decisions with significantly more confidence, clarity, and care.
Hiring When Everything Feels Unpredictable: How Startups Plan Headcount in Uncertain Times
Hiring used to follow a relatively predictable startup playbook: raise capital, grow headcount, scale fast.
Today, leaders are operating in a much more complicated environment where market conditions shift quickly, AI is changing team structures in real time, and companies are under increasing pressure to stay lean while still moving aggressively. The result is that hiring decisions now carry even more weight and getting them wrong can create expensive problems that are difficult to unwind.
You will walk away learning:
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How leaders determine whether a company is truly ready to hire
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When full-time employees make more sense than contractors or fractional support
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What types of work companies are commonly offshoring and where it can create challenges
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Common ways startups accidentally overhire during growth periods
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How to structure teams that can stay flexible as priorities change
The pressure to “scale fast” has not disappeared, but the definition of a smart team has changed dramatically.
Whether you are advising founders, building hiring plans, or navigating growth under tighter constraints, this session is designed to help leaders think much more intentionally about how and when they build teams in a constantly shifting environment.
Your Onboarding Process Is Basically Vibes: How Startups Ramp New Hires Without Big HR Teams
Most startups do not have polished onboarding programs, detailed training systems, or entire People teams dedicated to employee experience. What they do have are new hires who need context quickly, managers juggling too many responsibilities, and teams trying to get people productive without overwhelming them or accidentally leaving them completely lost.
This session focuses on how onboarding actually works inside lean, fast-moving startup environments - and how small, intentional systems can create a significantly better experience even without formal infrastructure.
You will walk away learning:
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What matters most during the first 30, 60, and 90 days of onboarding
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Common places where new hires lose clarity or momentum
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Who should actually own onboarding responsibilities inside a startup
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How managers can onboard effectively without formal HR infrastructure
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What onboarding processes are worth building early and what can wait
Good onboarding does not require a massive People team or a perfectly documented process. It requires clarity, intentionality, and enough structure to help people succeed without slowing the company down.
Whether you are a founder, People leader, or manager building processes as you go, this session will help you think more strategically about how to onboard effectively in messy, real-world startup environments.
Your Culture Is Showing: Building High-Performance Teams Without Burnout
Startup culture is rarely defined by a mission statement hanging in Notion. It shows up in the small, repeated behaviors teams normalize every day: who gets rewarded, how managers handle pressure, whether late-night Slack messages are expected, how meetings run, and what behaviors leadership quietly tolerates when things get stressful.
Over time, these patterns become the real culture, whether the company intended them or not.
You will walk away learning:
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What the strongest real-world signals of company culture actually are
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How unclear expectations contribute to burnout and team friction
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What behaviors leadership teams unintentionally reinforce under pressure
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How burnout tends to surface before people openly talk about it
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Where inconsistent management standards create cultural problems
Culture is not built through slogans, it is built through repeated behaviors and decisions.
Whether you are supporting a founder-led startup or helping a scaling company mature its management practices, this session is designed to help People leaders recognize the cultural patterns shaping their teams long before they become much harder to fix.
Your Interviews Are Running on Vibes: How to Build Better Hiring Interviews
A surprising number of startup interviews still operate on vibes, gut instinct, and whether the candidate “felt like a fit.” The problem is that inconsistent, unstructured interviews are often bad at predicting performance and even worse at reducing bias.
This session focuses on how hiring teams can design interviews that are clearer, more consistent, and significantly more intentional without creating bloated corporate hiring processes nobody wants to use.
You will walk away learning:
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What hiring teams should actually be assessing during interviews
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Common places where bias unintentionally enters the interview process
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How to structure interviews around clear evaluation criteria
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Ways to write stronger, more focused interview questions
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How to align interviewers around consistent expectations and scoring
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What makes interviews more predictive of long-term success
Most interview processes are not intentionally designed, they simply evolve over time. This session is designed to help People leaders, hiring managers, and startup teams move from intuition-driven interviewing toward a more thoughtful, repeatable process that leads to stronger hiring decisions and a better candidate experience overall.
Meet Rebecca Anders! Rebecca is one of the folks on the Startup Boston Organizing Team creating content for the People Ops Track. Look her up and connect with them on LinkedIn.