Play the Long Game: A Top Recruiter's Playbook for Hiring and Becoming a Product Leader

Lauren Ipsen began her career in broadcast journalism but quickly decided she did not want to be "the face of sadness". She stumbled into executive search and spent years at the boutique firm Daversa Partners, mostly on consumer mobile build-outs for companies such as Twitter, Reddit, TaskRabbit, Nextdoor and Postmates. A small slice of her work covered stranger territory, including autonomous helicopters and robotics.

A client then recruited her to join as the first recruiting hire and build the talent function from scratch. She enjoyed operating, but missed working with many founders and watching the market. That pulled her to General Catalyst, where she now supports the consumer and crypto portfolio and says her time splits roughly 50/50 between networking and working directly with portfolio companies.

Lenny asks why so many of the best recruiters are moving to venture funds. Ipsen says it is definitely not about pay. She points to the volatility of search, where every three wins bring four more things to chase, and to the risk of betting on one in-house company in an uncertain market.

The biggest mistake Ipsen sees from founders hiring a first senior product leader is being distracted by shiny objects. A former CPO of a household-name company looks impressive, but those leaders are often far from the work and rely on a team of executors. An early-stage company then has to hire that team on top.

She prefers candidates closer to the work, people who can act like a PM one day and lead the next. She does not claim senior leaders lack hunger, and some come to startups because they miss building. But she leans toward people with something to prove, and notes that a leader's last five years may have been spent on team building, reviews and vision rather than the experiment-driven product work typical of pre-IPO companies.

Early in her career she chased "whales" to prove herself, and she now sees that as the wrong instinct. Being the best talent in the world does not make someone the best talent for this role today.

Product leaders come in many flavours, Ipsen says, so founders must decide where the person should "major and minor" and where they should spike. Should they lean into design, act as a very senior PM while building a team, or own long-term vision? She often sees boards demand a head of product without anyone knowing what the role is for, which she calls a search that is doomed from inception.

Her fix is to work backwards from the outcome: what is the mandate, and what does a person crushing it look like? Lenny adds the 90-day test and asks what the hire will do in the first few months. Ipsen agrees, and also asks what the person should be doing in a year, in two years, and through to an IPO.

She sees three common buckets of product leader: platform and infrastructure, core or consumer product including UX and design, and specialists in areas like growth or monetisation. Hiring one person to do everything creates a "unicorn" nobody can find. If you need someone imminently for ads, she says, hire for that and find the head of product later.

On titles, she says many startups avoid C-level and VP titles until around Series C or D, so head of product usually means the most senior product leader. Lenny's takeaway for early-stage companies is to start with head of product and avoid over-promising, since the last thing you want is to demote someone.

Asked what founders should do a year ahead of a product leadership hire, Ipsen says to always keep a pulse on the market, whether hiring or job hunting. Know which companies are thriving and which individuals are well-regarded builders with strong references. She encourages founders to chat with people who represent what good looks like and to bring them in as advisers.

Founders can simply say they have no agenda and want to meet great people. In her experience this flatters people, and executives are often glad of a break from day-to-day monotony. She calls the best hiring founders long-game players: at Daversa, landing a VP of engineering took a seven-month courtship that began with advising and structuring conversations rather than a formal interview.

There is no fixed time budget. Some searches end after calling three people, while others take months, and if you are in an active search it should consume your time. What matters is whether the hours move the needle, since blind LinkedIn messaging will not find the best of the best. Lenny recalls Airbnb meetups where each engineer was assigned a target guest to look after.

When a search starts, Ipsen taps about five product leaders she admires and asks who the best people they have worked with are. She trusts they would never introduce someone less qualified, so she avoids guessing by quantity and cold-calling strangers for back-channel references. Founders can use the same approach with investors and board members, who can point to one or two people who can point to three or four more.

Cold outreach is still worth doing if someone looks amazing, especially if framed as an open conversation rather than a poaching attempt. But if you are on a deadline, she says it is a poor use of time without knowing which companies and teams were strong during a given period. Lenny shares a tactic of hiring from companies known for excellent sales and targeting lieutenants, and Ipsen says "yes and no": a strong brand has weak links and people who rode the wave, so start with market mapping and then go a layer deeper.

Her favourite placement was Alex Strand, VP of engineering at IRL. He had built Amazon Prime Day and a core messaging platform at Snapchat, and was reluctant to leave. She says he moved within two weeks despite a seven-month push to a start date, and she later joined IRL herself.

Turning to the product-person side, Ipsen says breadth is critical for anyone who wants to become a product leader. That means touching platform, user-facing and other areas, rather than specialising in one thing. Specialists in growth or ads are still valuable, she says, but breadth maximises options. She also advises always keeping the window open to the market, so you are never running out the door and can be selective.

Lenny worries about people hopping between fancy companies to collect logos. Ipsen agrees that logo collecting is something you never want to be known for, and recruiters are trained to spot candidates who do not give opportunities a full chance. She also warns about being loyal to a fault when a company is tanking, and says it is "an art and a science" to know when to stay.

Her test for how long to stay is whether you can point to a fingerprint: something you led that others can speak to and are proud of. If cross-functional leaders and your team sing its praises, you left the place better than you found it. Reference checks happen constantly and tech is small, so leaving well matters.

Product leaders sometimes upset people, but Ipsen says disagreement need not damage a reputation if it is handled in a fact-first, less emotional way. Slam-dunk references with nothing negative are rare, glaring problems surface fast, and the mixed middle is the hardest to judge.

On reference calls, Ipsen says to probe harder than feels necessary. Ask why you would not hire the person, what their real weaknesses are, whether the referee would hire or report to them again, and whether they would endorse them with their name attached. Even a slight pause is informative. Back-channel references reveal more than provided ones, which she compares to an Instagram Reel versus the photos you are tagged in.

Short stints are a red flag only when they repeat, she says, and in the current market a single short tenure should not disqualify anyone. She finds it a bigger red flag when people hide a company they left within a year, or label failed ventures as advising, or leave a role listed as current long after leaving. Executives, she adds, are increasingly judged by conversations and references rather than résumés.

For interviews, she warns PMs not to blame engineering or other teams for missed deadlines. Candidates should speak honestly about strengths and growth areas, and practise their story, since many only learn to tell it well by their tenth interview.

Lenny asks whether leaders should plan their path backwards from a goal. Ipsen says someone aiming to be CEO might move from product into a GM role with a P&L, but she warns against letting titles or valuation bubbles derail a role where you are learning and making an impact. A goal like "chief product officer" is vague without asking "of what?"

On what recruiters get wrong, she says it is forgetting they are dealing with human beings. Having been a candidate herself, she found transactional calls grating. She advises listening and remembering what people say, such as not pitching crypto to someone who ruled it out, or not chasing them before a vest date they mentioned. Trust, once lost, is impossible to regain.

She suggests engaging recruiters or talent advisers proactively, using your venture backers, and considering an outside firm around Series B. To evaluate a recruiter, brief them and ask them to repeat back what they heard. Then ask for candidate ideas in real time, to see where their mind goes and how quickly you can calibrate.

Her closing advice is to treat people like human beings, build rapport and play the long game. In the lightning round she mentions favourite interview question as strengths and weaknesses, looking for honesty rather than "I work too hard" answers.