Learnings from Attio, Hex, and Segment: Hollie Wegman on Building the Operator Muscle
Operator-Exec Hollie Wegman shares what four years running Attio taught her about building AI-native startups. We discuss how everyone is an Operator now.
Hi, I’m Jan. After years as a Chief of Staff and Operations Lead at companies like Airbnb, I started The Operator to give a voice to the people leading, growing, and shaping high-growth tech companies. Every few weeks, I share stories from Operators who have helped build some of the most exciting organizations in tech.
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Setting the Stage
Hollie Wegman has had a front-row seat to some of the most interesting company-building stories of the last decade. As VP of Marketing at Segment, she helped scale a company all the way to the $3.2B acquisition by Twilio. Hollie also worked with Redpoint Ventures as an Entrepreneur in Residence, advising dozens of startup founders. Most recently, Hollie worked with Attio, the AI-native CRM that raised $52M led by GV, as an advisor and COO.
Hollie recently departed Attio to invest in and advise AI startups. We connected through a mutual connection at Peak XV, and I was keen to learn what someone with Hollie’s breadth of experience sees when she assesses how startups should be built today.
This conversation goes deep on what actually changed about the Operator playbook in the AI era.
From Marketing Leader to COO: Hollie’s journey
Hollie started her career in Marketing, then over time moved into more general company operations topics. Her transition from Marketing Leader to COO happened organically:
“I came into Marketing via Analytics, so I’ve always had an analyze-the-business lens. As a leader of any function, you should be thinking about the company and what they’re trying to accomplish: what market forces and opportunities are in play. When you build that way, there’s a natural drift towards running not just your function, but also running the company.”
At Attio, this drift followed a familiar pattern. She joined as an advisor before the Series A round, working closely with a 15-person team on positioning, pricing, packaging, and launch strategy. As the company found product-market fit and the challenges shifted from finding PMF to scaling, her scope expanded into people, talent, legal, and support.
Asked about the COO as a role blueprint and title, Hollie was very clear:
“I don’t think it matters what position you have in a company. If you’re on a rocket ship, it doesn’t matter which seat you’re sitting in. If you’re willing to take on different projects and learn, the title doesn’t matter at all.”
She frames the business itself in three pillars: engineering/product/design, go-to-market or GTM (marketing, sales, support), and G&A (finance, legal, people). Entering through GTM gave her visibility into the revenue side while bumping into finance, legal, and other operational functions. It’s a natural springboard into broader leadership though Hollie admits that it doesn’t teach you engineering or product.
Running an AI-native startup: Jazz, Not Symphony
One part of operating startups I find most interesting are inner company operations, basically the structure, systems, and rituals that keep a company running. Traditionally, those items would fall into the realm of a COO or Chief of Staff - yet more and more startups have changed the way they operate entirely (check out how Linear thinks about this).
When I asked Hollie to walk me through the cadences, OKRs, and operating structures at Attio, she pushed back on the premise entirely. This was one of the more refreshing parts of our conversation:
“In my earlier career, we were trained that everything must be a rational system. You need OKRs, you need to cascade them, you need notes and actions. All this stuff is really great when you want to orchestrate a big company. But in this new era where AI is automating a lot of tasks, instead of constructing these tightly wound symphonies, you have to think of it like a jazz artist.”
No rigid weekly cadences or cascaded OKR trees. Instead, Hollie describes an environment of radical ownership where people have deep context, carry big ideas autonomously, and are supported to deliver without being told how to do every single thing:
“I like to work in creative teams, solving problems through brainstorms, spending time together synchronously and asynchronously: stand-ups, huddles, one-on-ones but less formulaic. Creating an environment where somebody feels they have a lot of context and they can carry big ideas through.”
On KPIs and particularly North Star metrics, Hollie doesn’t dismiss them but challenges the conventional approach:
“If everything in the organization is orchestrated around a number - say 10 million - well, what if you could have done 20 million? You orient towards something and that’s the most you’re going to hit. You do need North Star metrics, but you have to keep pressure testing what’s possible.”
Even VCs, she says, are on board with this looser approach: they expect to see numbers and know what’s happened, but they’re not asking for multi-year plans. Planning a quarter ahead feels reasonable. A year ahead feels like folly.
The Hardest Part of the COO Role That Nobody Talks About
One of the sharpest moments of our conversation came when I asked Hollie about the unspoken challenges of being a COO:
“If you’re a really good COO, everything feels invisible. People just get hired, legal just happens automatically, support tickets come and go, all the customers are happy. All the things within your purview just sort of magically happen. The hardest part is that there’s a lot of machinery in making that happen and making it feel invisible isn’t as easy as it looks.”
She describes a psychological tension that any Operator will recognize: the better you do your job, the less visible your contribution becomes. And when people view operational work as table stakes, it can be tough to sustain.
Her advice for avoiding the trap? Build thinking time into your calendar:
“Once a month or so, take a couple of days where you don’t have a day full of meetings. Allow yourself to sit and think. Jump on a huddle with someone, maybe not even in your department. Apply that kind of radical curiosity and reach across the organization to figure out what people are doing. Then, brainstorm, leave space for ideas, challenge the way we do things.”
The engine room metaphor came up naturally in our conversation, and it stuck: a great Operator knows the gears of a company intimately, but they can’t afford to stay inside them all the time.
The AI-Native Org Chart or Hiring Frontier People
Hollie’s perspective on how AI is reshaping the startup org chart comes from operating inside it at Attio and now supporting founders across a portfolio of AI companies.
People, she insists, are still critical yet the ideal hire persona has fundamentally changed:
“The kinds of people we’re looking for are people who almost have a founder-ish perspective. They’re very happy to grab a problem, use AI to build workflows, and amplify their ability to get things done. [They’re] able to jump in, grab other people, create teams to tackle problems [...], crossing departmental boundaries.”
She distills the ideal profile into three attributes: relentless problem-solving, the ability to create their own operating principles on the fly, and bold, unexpected ideas paired with the ability to MVP them.
“They’re like frontier people blazing a trail. Not only do they have really good ideas, but they can go build it. It’s a founder mentality.”
On the GTM side, she sees the biggest shifts in how much a small team can now accomplish. Writing, workflows, website building, customer support are all areas where AI has created what she calls “a huge assistance layer.” At Attio, a large percentage of support volume could be handled by AI with the right operating practices in place.
Hollie captured this shift in a LinkedIn post “traditional work is 9-to-5, AI startups work 9/96, agents work 24/7”, hinting at a deeper structural shift. Software is no longer built by humans for humans. Increasingly, it’s built for agents to use. And that changes everything about how you think about product, distribution, and operations.
“We’re All Operators Now”: The Changing Role of the COO
Having worked across company stages and verticals, I was keen to better understand the changing COO role. Here, Hollie shared perhaps the most provocative take from our conversation:
“I think the role of every person working in business is changing. This is a hot take, but they’re becoming more COO-like. As AI takes a lot of automation out of the work, the rigid team structures lighten. We all have to work cross-functionally. We all have to work for the company’s goals rather than necessarily in Finance, or in Marketing.”
The traditional core responsibilities of a COO, staying above the day-to-day, understanding macro trends, figuring out how to move the whole business, are becoming a baseline expectation for everyone. AI gives everyone the tools to operate that way. The question is whether people have the right mindset and agency.
Lessons from Segment, Miro, and Hex
Hollie has worked with and advised companies at wildly different stages and in different categories. At Segment, she was there right up to the Twilio acquisition. At Hex, she got an early look at how AI could be woven into the product experience. At Around (later acquired by Miro), she worked closely with a small team. Across all of them, she sees two common threads in the ones that succeed: deep customer focus, and the ability to react to the market fast:
“All of the people in leadership in these companies are really well tuned to the market and really well tuned to the customer. And they’re all brand-centric: they want to create a feeling about why it’s exciting to use the product, not just a rational argument.”
At Segment specifically, the quality of the team left a lasting impression. She describes it as being surrounded by people so talented that simply listening and spending time with them put you on a constant learning journey. At Hex, the takeaway was slightly different: seeing early how AI could become native to the product experience rather than an afterthought. Each company taught her something distinct, and she carries those lessons across every advisory and investment she makes today.
Given Hollie’s fantastic marketing background, I wanted to understand how she sees the role of a strong brand in the software space. Hollie offered a compelling duality:
“As long as a human is buying software, there’s always not just a rational frame. Brand matters because brand is what feeling you have about a company.
There is a second world: if agents are the primary users of software, are agents eventually going to become the primary consumers of software? In which case, I don’t think an agent is going to care about the brand. It’s going to ruthlessly pick on who has the best price and gets the job done.”
In the near term, however, and today’s buying patterns, Hollie is certain that brands are definitely going to matter.
Patterns Across AI Startups
After four years in the COO seat, Hollie has shifted to investing in and advising AI startups. The vantage point is different and in some ways, richer. Instead of being deep in the gears of one company, she’s now looking across a portfolio and spotting patterns that are hard to see from the inside.
Her thesis is focused on the infrastructure layer: AI governance, AI search, and companies rethinking what software even looks like from first principles:
“Founders who are really questioning everything right down to the ground from first principles are the most interesting to me. Is it even software at all? We really have to question everything.”
Across the companies she works with, she’s found that what separates the great Operators from the okay ones has nothing to do with which operating framework they use. Some run tight OKR processes, others rely on pure improvisation. The difference is something harder to pattern-match for: intuition about when to switch modes.
“The pattern is there isn’t a pattern. The ones who [succeed] have the intuition to know when to switch modes from very structured to very unstructured and go after it relentlessly. Strong opinions, loosely held.”
She describes a tension in advisory work that any Operator who has moved between building and advising will recognize: you get to stay on the innovation layer without getting sucked into the weeds, but you know the details matter:
“There’s this temptation when you’re in advisory. You think, ‘if I could just get in the gears more, I could do more for the company.’ But in this era, it’s actually nicer to stay out of the operations completely.”
Her reasoning is pragmatic: the mechanistic, repetitive operational work is increasingly becoming commoditized as AI absorbs it. The strategic layer above, reading the market, connecting dots across companies, challenging assumptions from the outside, is where the real leverage sits right now.
Advice for Fellow Operators
Since The Operator newsletter is aimed at a technically-savvy Generalist audience, I was naturally curious to ask for Hollie’s advice for fellow Operators. Interestingly, Hollie writes her own newsletter called “Dear Operator,” and her definition of the audience tells you everything about how she sees the future:
“Dear Operator isn’t necessarily aimed at a COO or somebody in operations. The way I see the future is that everybody who works in a company is an Operator of AI. I’m thinking about the people working alongside AI for now, and eventually the people who are going to be the human in the loop for the agents.”
Her advice for staying relevant? It’s less about specific skills and more about a disposition:
“Curiosity. ‘How does that work? If I got that tool, how would it work? What if I got this other tool?’ It’s this deep curiosity and fearlessness. We can build software ourselves without being an engineer now. If you’re curious and fearless, those characteristics will carry you through.”
On career progression specifically, she has one clear message:
“I think people should stop thinking about that. I’ve taken roles called marketing that weren’t marketing. Think about how to build companies, think like a founder, and I think you’ll go very far.”
Thank You
Thanks for reading this issue of The Operator.
Hollie’s career arc, from marketing to working alongside VCs at Redpoint to COO of one of the fastest-growing AI startups to advisor/investor is a masterclass in the kind of adaptability that is so required in the AI-age. I especially appreciated her level of abstraction on where AI startups are going and how to stay relevant.
Big thanks to Hollie for this fantastic conversation. You can follow her work on Substack and connect with her on LinkedIn.
See you soon,
Jan
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This was great. Love learning more how our roles are changing and more! Thank you for this