LLenny's Podcast
← All episodes
Lauren Ipsen (Daversa Partners, General Catalyst)03 November 2022

Lessons from one of the world’s top executive recruiters

7Frameworks
15Insights

Frameworks in this episode

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 2

Hot Take10:00

The Biggest Mistake Founders Make: Chasing Big Names

The most common error early founders make when hiring their first senior product leader is getting distracted by shiny objects and huge logos like CPOs of Google or YouTube. Those senior people are often far from the actual work and rely on a team of executors underneath them. Founders with limited resources should instead target someone closer to the work who can operate like a PM some days and lead on others.

  • Big-name executives are often far from the day-to-day work and depend on a team of executors
  • Early-stage companies with limited resources shouldn't chase brand recognition hires
  • Target someone who can both operate as a PM and build from a leadership perspective
  • Look for DNA, not just an impressive logo

it's really easy to be distracted by shiny objects and look at huge names if you want to find the cpos of Google and YouTube…

Lauren Ipsen · 10:00

oftentimes those individuals are pretty far from the work and have a great team of executors that they've put into place that are actually the…

Lauren Ipsen · 10:00
#hiring#product-leaders#founders#recruiting
Hot Take55:00

You Could Be the Chief Product Officer of Your Household

Wanting to be a "chief product officer" is meaningless without asking of what, since you could be the CPO of your household. Work backwards from a real goal, but don't let titles, valuation bubbles, or a shiny role at another company derail something that already feels good. If you're making an impact, learning, and excited, don't let an external title convince you your work isn't worthwhile.

  • "I want to be a CPO" is vague; of what, exactly?
  • Work backwards from a genuine goal, not from a title
  • Don't let titles or valuation bubbles derail a role that feels good
  • Impact, learning, and excitement matter more than a fancy new logo

you could be the chief product officer of your household

Lauren Ipsen · 56:30

don't allow titles or valuation bubbles or other things to derail something that feels good

Lauren Ipsen · 56:30
#career-advice#titles#goals#product-leaders

Explainer· 3

Explainer14:30

Nail Down the Mandate Before You Open a Search

Before kicking off a search, founders must get incredibly granular about what the person is coming in to do and what their mandate is. Too often boards push for a head of product without a clear reason, which dooms the search from inception. Define the outcome you're solving for, write the 90-day plan, and articulate what crushing it in the role actually looks like.

  • Work backwards from the actual outcome the hire is meant to solve
  • Don't hire a head of product just because the board says so
  • A search started without a clear mandate is doomed from inception
  • Define success: what does this person do in 90 days, a year, two years?

so you need to get incredibly granular on the front end around what is this person going to be coming in to do what's their…

Lauren Ipsen · 14:30
#hiring#search-process#founders#job-description
Explainer16:00

The Three Buckets of Product Leaders

Lauren buckets product leaders into three archetypes: platform leaders indexed on infrastructure, core/consumer product leaders (which can include UX and design), and specialists hyper-focused on growth or monetization. Founders get into trouble when they try to hire one person to do everything, which turns the role into a mythical unicorn. A clear org chart on the front end keeps the search honest.

  • Platform leaders index on infrastructure components
  • Core/consumer product leaders can include UX and design people
  • Specialists focus on growth, monetization, or a similar niche
  • Hiring one person to do everything creates an unhireable unicorn

there's platform product leaders or folks that are kind of more indexed on the infrastructure components there's folks that are typically focused on like core…

Lauren Ipsen · 16:30
#product-leaders#hiring#archetypes
Explainer49:30

The Resume Red Flag Worse Than a Short Stint

Recurring stints under a year are a red flag, but hiding those short stints from your resume is arguably worse. Because people fear the jumper narrative, they omit companies they didn't stay at for a year or claim they were "advising" when in reality they had two companies fail. Lauren's advice: be honest about your dates and tell your story with grace, because the omission itself is the bigger tell.

  • Recurring sub-one-year stints are a red flag, especially two or three times
  • Omitting short stints from a resume is almost more of a red flag than including them
  • People claim they were "advising" to hide companies that failed
  • Be honest about start and end dates; you can explain a bet that didn't work out

people will often because they're so afraid of that narrative they'll often not include on their resume companies that they didn't stay for a year…

Lauren Ipsen · 50:30
#resume#red-flags#career-advice#honesty

Story· 3

Story24:30

The Seven-Month Courtship of a VP of Engineering

At Daversa, the VP of engineering candidate they ultimately landed was a seven-month game of courtship rather than a formal interview process. They brought him in to advise, asked how he'd structure the org, and had him recommend other great talent. Skipping the transactional interview built a different level of rapport and trust, which is how you land incredible people.

  • Best hires can take many months of relationship-building, not a quick interview loop
  • Bring candidates in to advise and recommend talent before the formal ask
  • Avoiding a transactional process builds rapport and trust
  • Collaboration over formality is where the magic happens

when I was on the executive recruiting side of things at diversa the VP of engineering candidate that we ultimately landed it was a seven…

Lauren Ipsen · 24:30
#recruiting#hiring#long-game#story
Story26:30

Airbnb's Target-Engineer Tech Talk Tactic

At Airbnb, monthly engineering tech talks doubled as recruiting events: a target engineer would visit, and the existing engineers were given that person's profile and picture with the job of making sure they had a great time and convincing them to join. Lenny compares it to college sports recruiting trips. The target often had no idea, but the tactic worked great.

  • Monthly engineering tech talks were used as covert recruiting events
  • Existing engineers were assigned a target engineer to host and impress
  • It mirrors college sports recruiting visits
  • Staying top of mind and giving people a great experience worked

all the engineers get a Target engineer that is coming to vent like they get their profile in their picture and their job is to…

Lenny Rachitsky · 27:00
#recruiting#tactics#airbnb#story
Story33:30

Her Favorite Placement: Joining the Company Right Behind Him

Lauren's favorite placement of all time was Alex Strand, a rare high-EQ but still deeply technical engineering leader she placed at IRL. He'd built Amazon Prime Day and Snapchat's core messaging platform, and she convinced him to move in two weeks (though the start date ended up seven months out). She was so confident in the hire that she joined IRL herself to work alongside him, the ultimate stamp of confidence.

  • Alex Strand was an atypical high-EQ yet still very technical engineering leader
  • He'd built Amazon Prime Day and Snapchat's core messaging platform
  • She got him to decide to move in two weeks; the start date landed ~seven months out
  • She joined the same company to work alongside him as her ultimate vote of confidence

favorite placement of all time has got to be the VP of engineering that I placed at IRL

Lauren Ipsen · 33:30

I don't know how much more confidence you could instill in a Canada joining company than the recruiter also then joining the company

Lauren Ipsen · 35:30
#recruiting#placements#story#engineering-leaders

Tool· 1

Tool48:00

How to Actually Get Truth Out of a Reference Call

Provided references almost never come back negative, so you have to dig deep and ask hard questions: why would I not hire this person, what are their real weaknesses, would you hire or report to them again? Push past the canned "they work too hard" answer. Even the slightest pause is enough to make you think twice, so reading the room and probing harder than feels comfortable matters more than the words.

  • Provided references rarely come back negative; back-channels are a better source of truth
  • Ask: why would I NOT hire this person? What are their actual weaknesses?
  • Push past canned answers like "they work too hard"
  • Even a slight pause is a signal; read the room and probe harder than feels necessary

why would I not hire this person what are their biggest weaknesses and then if they give you like the typical oh they work too…

Lauren Ipsen · 48:30

even if you just sense the slightest pause that in itself will be enough to to kind of make you think twice

Lauren Ipsen · 48:30
#reference-checks#hiring#recruiting#tactics

Takeaway· 6

Takeaway12:30

"Best Talent" and "Best for This Role" Are Different Questions

A successful hire is about who is best for this specific role at this specific time, not who is the best talent in the market. Early in her career Lauren chased impressive executives to prove herself, but landing a whale doesn't mean that person can move the needle for the company today. The two questions are very different and conflating them dooms a search.

  • Ask who is best for THIS role at THIS time, not who is best in the market
  • Landing an impressive name is not the same as making an impact
  • The best talent in the world may not be the best talent for your company right now

I would say the general advice is who is going to be best for this specific role at this specific time not necessarily who is…

Lauren Ipsen · 12:36
#hiring#recruiting#product-leaders
Takeaway18:30

Head of Product vs VP vs CPO: When Titles Actually Matter

Startups are increasingly title-agnostic, with "head of" roles common up through C/D stage and VP/CPO titles appearing later at D and E. Unless it's a siloed company with multiple VPs, head of product, VP of product, and CPO generally mean the same thing depending on stage. Early-stage founders should start with head of product to avoid ever having to demote someone as the company scales.

  • Startups are more title-agnostic than in the past; "head of" roles dominate early
  • VP/director/CPO titles appear more at D and E stage
  • Head, VP, and CPO of product often mean the same thing depending on stage
  • Start early-stage roles as head of product so you never have to demote

if you're coming into a company and they say this is the head of product the VP of product or the CPO that all means…

Lauren Ipsen · 21:00
#titles#hiring#startups#product-leaders
Takeaway22:00

Keep a Pulse on the Market Before You Need to Hire

Whether or not you're actively hiring, you should always keep a pulse on the market so you know what good looks like. Founders should proactively meet great people with no agenda, get them involved in advising or the product before a specific need arises. Reaching out with genuinely no agenda makes people feel flattered and often eager to help.

  • Always know which companies are thriving and which individuals are building great things
  • Meet and involve great people before you have a specific opening
  • A "no agenda" approach makes people feel flattered rather than poached
  • Executives across the board are often glad for a conversation outside their day-to-day

regardless of whether or not you're hiring you should always be keeping a pulse on the market that is the most important thing

Lauren Ipsen · 22:00

by simply saying No Agenda I'm not trying to hire you tomorrow I just want to know great people and to be totally honest people…

Lauren Ipsen · 23:00
#networking#hiring#relationship-building#founders
Takeaway37:30

For PMs: Build Breadth, Don't Collect Logos

Product people aiming for leadership should prioritize breadth, touching many different components rather than specializing in one, unless they deliberately want to be a specialist. At the same time, logo collecting is a known red flag: recruiters are trained to spot candidates who jump from place to place without giving opportunities a full chance. But staying too long out of loyalty to a fault, past when the writing is on the wall, is its own trap.

  • Touch many components (platform, consumer, tools) to grow into a product leadership role
  • Specializing is fine if that's the deliberate goal
  • Logo collecting is a red flag; recruiters spot serial jumpers immediately
  • Being loyal to a fault and staying too long is also a mistake

it's so critical especially if someone has an end goal of wanting to step into a product leadership role to have been able to have…

Lauren Ipsen · 37:30

logo collecting is never something that you you know want to be known for and the first thing you're taught like entry level recruiting 101…

Lauren Ipsen · 41:00
#career-advice#product-managers#breadth#resume
Takeaway43:00

Leave Every Company Better Than You Found It

The tech world is tiny and people are constantly calling each other for references, so no matter how fired up you were leaving, it's critical to leave a place better than you found it. If a recruiter calls ten people from your org and none can speak to what you did, no news is not good news. You want a meaningful impact that others can point to.

  • Tech is small; people back-channel constantly regardless of how you leave
  • Leave every place better than you found it, seamlessly
  • If ten colleagues can't name your impact, that silence counts against you
  • Impact must be visible to others, not just something you're privately proud of

no matter how fired up you were leaving a company or what went sideways it is so critical that you try to leave the place…

Lauren Ipsen · 44:30

if I call 10 people that were a part of the same organization as someone during a given period of time and they can't speak…

Lauren Ipsen · 44:30
#career-advice#impact#references#reputation
Takeaway57:30

What Recruiters Get Wrong: Forgetting They're Human Beings

Recruiters earn their reputation by forgetting that candidates are human beings with lives, families, and ambitions outside their careers. Transactional recruiting, like pushing crypto roles on someone who said they never want one, or hitting up a candidate right before a vesting date they told you about, is tone-deaf. Start with a relationship, take notes, and remember that once you lose a candidate's trust it's impossible to get back.

  • Treat candidates as humans with lives and ambitions outside work
  • Transactional outreach and ignoring what people told you is tone-deaf
  • Take notes so you don't push crypto roles on someone who rejected them
  • Once you lose a candidate's trust, it's impossible to get it back

there's naturally people that forget that these are human beings that we're dealing with every single day that have lives have families have careers or…

Lauren Ipsen · 57:30

once you lose trust in a candidate it's impossible to get it back

Lauren Ipsen · 1:00:00
#recruiting#relationship-building#trust#long-game