Tip of the Spear: Lea Engelhardt, CEO of Paine Ventures

December 11, 2025

By The Artemis Fund
The Artemis Fund believes technology can create prosperity for all. With offices in New York, Texas, Massachusetts, and Nevada, Artemis leads seed rounds for companies creating resilient families, individuals, and businesses across the US.
Tip of the Spear is an interview series highlighting The Artemis Fund’s expert network. In this edition, we sat down with Lea Engelhardt, CEO of Paine Ventures, a fractional people and talent service for venture firms.

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Q: You started your career at Benchmark and later became Chief of Staff at a Series A startup. What did those early experiences teach you about how great companies work from the inside?
A: I always say my time working with Josh Reeves at Gusto was my version of business school. We went from roughly 10K to more than 300K customers, 20 to almost 2,000 employees, and about $8M to $200M in ARR. Because we were so small when I joined, a lot of roles didn’t exist yet, so I had direct exposure to parts of the business I’d never touched. My work required constant altitude-shifting — moving between strategy and very tactical execution — which taught me how to connect the two.
What stayed with me most was how intentional Josh was about culture and team-building. He was deeply connected to the people side of the company, and seeing that modeled at scale grounded my belief that founders set the tone. You can (and should) evolve how involved they are over time, but the underlying intention has to be there. Leaders who genuinely care about people and culture have an outsized impact on how a company grows.
Benchmark was a different lens. I interacted mostly with founders, so I didn’t yet see inside the engine of the companies themselves. I learned how GPs evaluate businesses, but I didn’t have the operating context to map it to. Moving into the startup world changed that. It was the first time I saw how teams are structured, how decisions get made, and why certain problems rise to the top. It made the “org chart” feel real and shaped how I think about company building today.
Q: You’ve worked with teams from 25 people to thousands. What patterns have you noticed in how companies evolve as they scale?
A: I tend to think about scaling in three buckets: profile, layering, and expansion — and where things break when companies don’t anticipate what’s coming next.
1. Profile
The kind of person who thrives at Seed or Series A is not always the same person who thrives at Series C or pre-IPO. Early stages reward generalists who can pick up anything. Later stages require specialists who’ve “seen the movie” and operate with more precision. Both profiles are valuable, but friction builds when companies treat that shift as a surprise rather than a developmental milestone.
I’ve also seen what happens when growth becomes a headcount exercise. When you scale from a few hundred people to nearly a thousand in a year, the operating systems, culture, and clarity of roles often can’t keep up. More people does not equal more output. When growth outpaces structure, you see misaligned expectations, unclear ownership, and a culture that feels stretched thin. Don’t scale a company faster than you scale the judgment of the people operating within it.
There’s also a natural morale cycle. Some early employees are builders at heart. When the work turns into scaling and optimization, they’ll naturally transition out. That isn’t a sign the “family” is falling apart,  it’s a sign the company is maturing. Those transitions deserve clarity and celebration.
2. Layering
At some point, the company can’t stay flat. You introduce managers, directors, and more structure — ideally not just because it’s time, but because the complexity of the business demands it.
This is where frontline managers become the backbone of the company. They carry the strategy, manage change, develop people, and translate leadership decisions into day-to-day execution. And they’re often doing this for the first time. If you don’t define what you expect from them and how you’ll support them, gaps compound quickly. Managers set the tone for how scalable the org really is. And remember, managers are also employees, they need space to process change before they communicate it.
3. Expansion
Expansion adds a different layer of complexity. When companies open new offices, there’s often a push for uniformity — same rituals, same norms, same culture. In practice, that can create more friction than cohesion.
What works is the opposite. Each office will naturally develop its own character based on the people, the rhythms, and the local culture. The goal isn’t to replicate headquarters everywhere; the goal is a shared backbone of values and behaviors, expressed differently in each environment.
When leaders embrace that, offices feel empowered rather than policed. When they resist it, teams feel disconnected or misunderstood.
A final point: AI changes the scaling equation. AI wasn’t a meaningful variable during my early operating years, but it is now. Headcount is no longer the default lever. Teams can stay leaner for longer, and the work that truly requires human judgment becomes clearer. The companies that scale well today will understand both kinds of leverage, human and AI, and design for them with intention.
Q: What do high-performing, low ego teams actually look like day to day?
A: One misconception is when to think about team building. Most companies focus on talent only when there’s an urgent need, which forces them into reactive mode. It’s like saying, “We need to deploy capital this quarter, so let’s invest in whatever we can get into.” No investor would operate that way, but leaders do it with hiring all the time.
When you only hire on a deadline, you choose from whoever’s available, not from the best possible talent pool. High-performing, low-ego teams are built long before the role opens. That looks like:
• Cultivating talent networks continuously
• Building a reputation people opt into
• Having someone explicitly responsible for the long-term shape of the team
Opening or closing a req is an activity. Building a team is strategy. Great leaders don’t confuse the two.
For companies that outsource recruiting, especially early-stage firms and funds, the key is choosing someone who deeply understands how your team operates: the personalities, the working styles, the quirks, the decision-making patterns. Low ego isn’t about finding “nice” people — it’s about putting the right people in the right roles for your environment. Ego friction is usually a misalignment problem, not a character flaw.
That’s the nuance my firm focuses on. The goal isn’t to surface a hundred possible candidates — it’s to identify the twenty who are not just great, but great for you.
High-performing teams tend to share traits: sharp thinking, hunger, resilience, and a willingness to do unglamorous work with clarity rather than ego. You build that by hiring for aligned ways of operating, not keywords.
Q: For lean teams, what’s the minimum viable system for performance management or goal-setting?
A: The biggest mistake is focusing on output instead of impact. Before you talk about metrics or OKRs, you should be able to answer three questions for every role:
• What impact is this person responsible for?
• What does success actually look like?
• How will we know, even loosely, if it’s happening?
If you can’t articulate that, it’s worth questioning why the role exists.
From there, the system can stay incredibly simple. You need clarity at three levels:
• Company goals
• Department goals
• Individual impact metrics that ladder up
Not everything needs to be perfectly quantifiable, but expectations should be crisp enough that people know whether they’re moving the business forward or just staying busy.
Companies often evaluate only the “what” — did someone hit the target, ship the project, check the box? But impact lives in the “how.” Did the work matter? Did anyone adopt it? Did it elevate the team or create cleanup downstream? Someone can hit every metric and still create cultural drag.
When we built performance frameworks at Gusto, one core principle was evaluating both dimensions:
• The outcomes a person drove
• How they behaved against the company’s attributes
A minimum viable system doesn’t need heavy process. It needs clarity, alignment, and a balanced view of what was accomplished and how it was accomplished.
Q: What’s a subtle signal that a team might be heading for trouble, especially in terms of leadership and management?
A: “Trouble” can mean a lot of things, but when I’m looking at managers and their teams, there are three areas that almost always surface issues early: how they drive the business, the health and quality of their team, and how they communicate and exercise judgment.
1. Business impact
Goals are a useful signal, but not in the simplistic “did you hit them or not?” way. I look for:
• Are the goals ambitious enough, or are they calibrated to be comfortably achievable?
• When goals are missed, is it due to poor execution or because the manager made a deliberate and correct call to redirect priorities?
• When goals are exceeded, is it because the team is exceptional or because the bar was artificially low?
Strong managers make sharp tradeoffs and communicate them clearly. You don’t want 100% goal attainment — that usually means the bar isn’t high enough.
2. Talent quality and team health
A manager’s ability to attract, develop, and retain strong people sets the ceiling on the team. If a manager consistently hires down, loses strong performers, or runs a team with quiet churn, the issue isn’t the market — it's leadership.
I look for:
• Who they hire and why
• Whether top performers choose to stay
• Whether the team’s energy is healthy or quietly deteriorating
Strong managers create upward pressure — better people want to join and grow.
3. Judgment and communication
This is the subtle one, but it’s where patterns start. Judgment is the glue between strategy and execution. When it’s strong, teams move with alignment. When it’s weak, you see misfires and friction long before performance metrics dip.
You can see it in:
• How clearly managers communicate up and down
• How they explain decisions and tradeoffs
• Whether they escalate issues early or wait until something breaks
• Whether their team operates with clarity or confusion
Across clients and past companies, the patterns almost always show up here first.
Q: What’s one trait you consistently see in resilient leaders that others might overlook?
A: The most resilient leaders I’ve worked with have one trait in common: they create change for themselves instead of waiting for the world to do it for them.
Most big shifts in life are reactive — a job loss, a crisis, a restructuring. You can grow from those moments. But the leaders who are truly resilient disrupt their own comfort before circumstances force it.
They ask themselves:
• Where am I too comfortable?
• What have I outgrown?
• What challenge would force me to level up?
And then they make those moves. They engineer periods of discomfort so adaptability becomes a muscle, not a reaction.
You see it in how they operate: they navigate ambiguity with curiosity, adapt quickly and bring their teams with them, and set the pace rather than resisting change. When uncertainty inevitably hits, they aren’t fragile — they’ve already built the capacity to reset direction and lead with steadiness. They assume change is coming and prepare accordingly.
Q: What trends in people strategy or org design are you most excited about right now?
A: AI is the obvious one, and the one I’m most excited about. But the way I think about it is simple: AI shouldn’t replace humans — it should make humans stronger.
The real value in our work is in psychology: understanding people, context, dynamics, and judgment. That’s the part I want to spend more time on. Everything else — the admin, the logistics, the repetitive tasks — is what should be automated so we can stay focused on the higher-order thinking.
When I’m evaluating a venture candidate, I’m not just scanning a resume. I’m thinking:
• Which fund were they at and what was happening there at the time?
• Who did they work under and what were those people known for?
• What deals did they see, how were those decisions made, and what did they learn from the environment they grew up in?
There’s nuance in that evaluation that AI isn’t ready to replicate. A resume reveals chronology, not cognition. It tells you where someone has been, not how their brain works. The meaningful insights live in the context — the stories, decisions, and environments that shaped them.
AI can accelerate everything around that work. But the core of people strategy — understanding who someone is and how they’ll shape a team — remains profoundly human.
Q: What’s the best piece of career advice you’ve ever received?
A: The best advice I’ve ever received came during a low moment at Gusto when I was ready to quit on impulse. A colleague told me, “Don’t make long-term decisions over short-term emotion.” It was simple — and exactly right.
I think about that line constantly, especially when it comes to hiring. Leaders hit a point of exhaustion or overwhelm — no bandwidth, too much on their plates — and the instinct becomes, “I just need someone.” That’s how long-term hires get made from temporary feelings. And those decisions almost always create more problems later.
Adding someone to a small team is one of the most consequential decisions a leader makes. If the motivation is to relieve today’s stress, you're likely to regret it. It’s far better to pause and ask:
• What problem are we actually trying to solve?
• Is hiring the right solution?
• If so, what would a long-term, high-quality solution look like — not just the fastest fix?
That advice has shaped decisions well beyond work, too. It’s become a grounding principle: don’t let short-term emotion dictate long-term outcomes.
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