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Melissa Tan (Webflow, Dropbox, Canva)18 June 2023

Building high-performing teams

9Frameworks
15Insights

Episode overview

Melissa Tan explains how clear goals, a meaningful mission, results orientation, collaboration, ownership, and fun contribute to high-performing teams. Drawing on Dropbox and Webflow, she argues that direct feedback and sustained investment in people can coexist with rigorous accountability. She also covers product-manager interviews, first-principles thinking, growth-team operating models, and how companies should approach their earliest growth hires.

Key ideas

  • High-performing teams need clear goals and success metrics, a motivating mission, a team-first culture, individual ownership, and room for fun.
  • Leaders can care deeply while remaining results-oriented by giving direct, work-specific feedback, stating supportive intent, and helping people meet explicit goals.
  • Internal talent development preserves institutional knowledge and reduces the risk involved in bringing outside leaders into a scaling company.
  • Melissa’s PM interview process combines live problem-solving, competency-focused interviews, and a role-relevant presentation preceded by a feedback-rich preparation call.
  • First-principles thinkers ask context-building questions, form their own mental models, and revise those models when new evidence appears.
  • Growth teams should derive experiments from their own data and customer research, define precise hypotheses, and right-size tests to the company’s scale.
  • A cross-functional “flying formation” should clarify decision roles through DACI, metric ownership, meeting cadences, and quarterly planning.
  • After product-market fit, an early growth hire often resembles an analytical, creative portfolio manager testing acquisition channels rather than a narrow specialist.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Communication4 steps

Care Deeply, Challenge Directly — The Feedback Script

Three moves that let hard feedback land as care instead of criticism

Read →
Mindset4 steps

First-Principles Thinking as a Hiring Filter

Build your own framework from context instead of importing one — and hire for it deliberately

Read →
Leadership4 steps

Flying Formation

Define cross-team roles (DACI) plus operating rhythms before growth ships anything

Read →
Influence5 steps

Organic Mentorship Sourcing

Never ask 'will you be my mentor' — pick managers whose success depends on yours, then bring real problems

Read →
Entrepreneurship5 steps

The First Growth Hire as Portfolio Manager

Hire acquisition first, and hire for attributes over channel expertise — expertise causes false precision

Read →
Leadership5 steps

The Five Ingredients of a High-Performing Team

Clear goals + a why, results culture, team-first, ownership, and fun — in that order

Read →
Leadership3 steps

The Ownership Engine

Ownership is manufactured by scope design first, culture second, and leader accountability third

Read →
Leadership4 steps

The Prep-Call PM Interview Loop

Coach the candidate before their final presentation — how they use your feedback is the real signal

Read →
Leadership5 steps

The Talent Development Lifecycle

Develop people across five stages: fit, ramp, early wins, visibility, lifelong relationship

Read →

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 9

  • Melissa TanMentionsMelissa was the long-time head of growth for Dropbox's B2B business. She was also their first growth product manager.

    “Today my guest is Melissa Tan.”

    ▶ Watch at ~0:30approx.
  • Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter

    “Today my guest is Melissa Tan.”

    ▶ Watch at ~0:30approx.
  • Oliver JayMentionstwo that really stand out are from Dropbox, Oliver Jay, he goes by OJ, and GC, Laney

    “two that really stand out are from Dropbox, Oliver Jay, he goes by OJ, and GC, Laney.”

    ▶ Watch at ~21:00approx.
  • Sheryl SandbergCoinedI was at a fireside chat with Cheryl Sandberg once at Airbnb

    “I think Sheryl Sandberg wrote this in in in her book Lean In”

    ▶ Watch at ~26:00approx.
  • Tim FerrissMentionsCited for his fear-setting framework and as an influence on Paul Millerd's five-episode podcast experiment.

    “Tim Ferriss talks about that, too. He's like, never ask someone to be your mentor.”

    ▶ Watch at ~27:30approx.
  • Kim ScottCoinedI think radical Candor by Kim Scott is just incredible

    “Kim Scott was at Dropbox for a short period of time.”

    ▶ Watch at ~42:00approx.
  • Abby KuzminovCoinedAbby Kuzminov who was on my team at Dropbox

    “I wrote actually an article for the YC blog a few years ago with with Abby Kuzminov who was on my team at Dropbox”

    ▶ Watch at ~50:30approx.
  • Simon SinekCoinedAuthor of Start with Why

    “The first one is Leaders Eat Last. I really like that leadership book. Um I sign them Simon Sinek.”

    ▶ Watch at ~1:10:30approx.
  • Michael JordanMentionsMichael Jordan used to say that you know I've failed over and over and over and over again

    “a new movie I just watched last night called Air which is about how Nike got Michael Jordan signed”

    ▶ Watch at ~1:11:00approx.

Resources · 35

  • RoMentionscompany

    “Canva, Grammarly, Miro, and Ro helping them with their growth strategy and helping them build their growth teams.”

    ▶ Watch at ~0:30approx.
  • Lenny's PodcastCoinedpodcast · Lenny Rachitsky

    “Welcome to Lenny's Podcast where I interview world-class product leaders and growth experts”

    ▶ Watch at ~0:30approx.
  • MiroUsessoftware · Miro

    “having been fortunate enough to work with great companies like Canva, Grammarly, Miro, et cetera.”

    ▶ Watch at ~4:30approx.
  • WebflowUsessoftware · Webflow

    “Over the last couple years I've been at Webflow building out the growth team there.”

    ▶ Watch at ~4:30approx.
  • CanvaUsescompany · Melanie Perkins, Cliff Obrecht, and Cameron Adams

    “having been fortunate enough to work with great companies like Canva, Grammarly, Miro, et cetera.”

    ▶ Watch at ~4:30approx.link ↗
  • GrammarlyUsescompany · Grammarly

    “having been fortunate enough to work with great companies like Canva, Grammarly, Miro, et cetera.”

    ▶ Watch at ~4:30approx.
  • LinkedInRecommendswebsite · LinkedIn

    “Definitely, LinkedIn is a good place. I I check my LinkedIn, so feel free to reach out there.”

    ▶ Watch at ~6:00approx.
  • BoxMentionscompany

    “And then Box came around and did that really well”

    ▶ Watch at ~7:00approx.
  • DropboxMentionscompany · Drew Houston and Arash Ferdowsi

    “having been at Dropbox for close to 5 years, I I did a lot of reflection while I was there.”

    ▶ Watch at ~7:30approx.
  • AtlassianMentionscompany

    “I imagine like look at Jira and Atlassian, they're just all product-led and that's amazing.”

    ▶ Watch at ~11:30approx.
  • JiraMentionssoftware · Atlassian

    “I imagine like look at Jira and Atlassian, they're just all product-led and that's amazing.”

    ▶ Watch at ~11:30approx.
  • FigmaMentionssoftware · Figma

    “And I think also about Miro or Figma, those also are a very viral products.”

    ▶ Watch at ~12:30approx.
  • Lean InMentionsbook · Sheryl Sandberg

    “I think Sheryl Sandberg wrote this in in in her book Lean In”

    ▶ Watch at ~26:00approx.
  • BarcelonaMentionsplace

    “I got to work with Typeform in Barcelona and then someone at Typeform introduced me to Canva.”

    ▶ Watch at ~28:00approx.
  • TypeformUsescompany

    “I got to work with Typeform in Barcelona and then someone at Typeform introduced me to Canva.”

    ▶ Watch at ~28:00approx.
  • LoomRecommendssoftware · Loom

    “One recent hack I have is having folks in the team create looms that they can share with different leaders at Webflow.”

    ▶ Watch at ~40:30approx.
  • Radical CandorRecommendsbook · Kim Scott

    “We're going to link to that book if folks don't know about it. I love it.”

    ▶ Watch at ~42:30approx.
  • YC BlogUseswebsite · Y Combinator

    “I wrote actually an article for the YC blog a few years ago with with Abby Kuzminov”

    ▶ Watch at ~50:30approx.
  • DACIRecommendsother

    “A DACI um is a framework to think about the different roles on the team on a project right or an area”

    ▶ Watch at ~54:30approx.
  • ReforgeRecommendscompany · Brian Balfour

    “find just a really smart person early in their career, have them take a Reforge class, have them soak up everything.”

    ▶ Watch at ~1:02:00approx.
  • HBOMentionscompany

    “This one isn't super recent but Winning Time on HBO.”

    ▶ Watch at ~1:10:30approx.
  • Leaders Eat LastRecommendsbook · Simon Sinek

    “The first one is Leaders Eat Last. I really like that leadership book.”

    ▶ Watch at ~1:10:30approx.
  • The Untethered SoulRecommendsbook

    “two non-career related books is The Untethered Soul. It really has taught me a lot about being present.”

    ▶ Watch at ~1:10:30approx.
  • The Four AgreementsRecommendsbook

    “And then also The Four Agreements which is like a very short and easy read but good principles to live by.”

    ▶ Watch at ~1:10:30approx.
  • Winning TimeRecommendstv show

    “This one isn't super recent but Winning Time on HBO. It's about the LA Lakers during the '80s and the Showtime era.”

    ▶ Watch at ~1:10:30approx.
  • Los Angeles LakersMentionscompany

    “It's about the LA Lakers during the '80s and the Showtime era.”

    ▶ Watch at ~1:10:30approx.
  • AirRecommendsfilm

    “You will love a new movie I just watched last night called Air which is about how Nike got Michael Jordan signed”

    ▶ Watch at ~1:11:00approx.
  • NikeMentionscompany · Phil Knight and Bill Bowerman

    “Air which is about how Nike got Michael Jordan signed”

    ▶ Watch at ~1:11:00approx.
  • ChatGPTRecommendssoftware · OpenAI

    “I feel like everyone's saying this but ChatGPT. I feel like it has really changed everything.”

    ▶ Watch at ~1:12:00approx.
  • Webflow UniversityRecommendscourse · Webflow

    “basically watching our university videos which is where we teach Webflow while also building in the designer.”

    ▶ Watch at ~1:13:00approx.
  • Figma to Webflow pluginRecommendstool · Webflow

    “our Figma to Webflow plugin which is you can take a Figma design um and then convert it to Webflow”

    ▶ Watch at ~1:13:00approx.
  • TwitterMentionswebsite · Twitter

    “Folks can find me on LinkedIn, also on Twitter MelissaMTan.”

    ▶ Watch at ~1:13:30approx.
  • Apple PodcastsMentionssoftware · Apple Inc.

    “you can subscribe to the show on Apple Podcasts, Spotify or your favorite podcast app.”

    ▶ Watch at ~1:14:00approx.
  • SpotifyMentionssoftware · Spotify

    “you can subscribe to the show on Apple Podcasts, Spotify or your favorite podcast app.”

    ▶ Watch at ~1:14:00approx.
  • lennyspodcast.comMentionswebsite · Lenny Rachitsky

    “You can find all past episodes or learn more about the show at Lennyspodcast.com.”

    ▶ Watch at ~1:14:30approx.

Spot an error or want something removed? Request a correction or removal.

Insights & moments

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

Myth Buster· 1

Myth Buster15:30

Caring Deeply and Driving Impact Aren't Mutually Exclusive

Melissa pushes back on the idea that leaders must choose between caring about people and driving results. She runs a very results-oriented culture where success is clearly defined and measured, and argues people actually appreciate knowing how they'll be measured. Supporting career growth and demanding results coexist.

  • As a growth leader, everything is measurable for better or worse
  • People appreciate clarity on what success looks like and how they'll be measured
  • She breaks goals down into individual levers so success is clear per person
  • A leader's role is to support career growth AND help people hit their goals

“I don't think that they are mutually exclusive of each other”

Melissa Tan · 16:00

“something that they actually appreciate is knowing what success looks like and knowing how they'll be measured.”

Melissa Tan · 16:30
#leadership#results-oriented#management#growth-teams

Explainer· 6

Explainer11:30

When to Start Leaning Into Sales vs. Product-Led Growth

Melissa explains that most companies lean heavier into either sales or product-led, not both at once. The signals product-led is right for you: an intuitive product with a low learning curve and a viral component. As larger self-serve customers knock on your door demanding enterprise features, you collect the roadmap for a later sales motion.

  • Product-led works when the product is intuitive to onboard with a low learning curve (no human needed)
  • A viral component (Dropbox, Miro, Figma) is core product-led DNA
  • Large self-serve companies asking for SSO and enterprise-grade features signal when to build the enterprise motion
  • Some companies start enterprise/sales-first and later try to shift to a more accessible product-led motion
  • Figure out how consumer and B2B journeys fit together as early as possible

“There's a low learning curve so you don't need a human to onboard the user.”

Melissa Tan · 12:30
#product-led-growth#sales#go-to-market#enterprise
Explainer20:30

Why She Develops Talent Internally Instead of Hiring Outside Experts

Melissa's case for growing people from within: it's personal (mentors invested in her when she struggled early in her career), and it de-risks scaling. Institutional knowledge and 'founder intuition' extend to early employees who have deep context on the user, making internal promotion a smoother, lower-risk transition than external hires.

  • Her passion for developing people comes from mentors who invested in her (she names Oliver 'OJ' Jay and GC Laney)
  • The school-to-work transition into ambiguity was hard for her; mentors helped
  • Founder intuition extends to early employees who've built deep user and company context
  • Developing internal talent de-risks scaling versus the many unknowns of an outside hire

“the more that you develop talent within the company, the smoother the transition is versus bringing someone from the outside where there's just a lot…”

Melissa Tan · 22:00
#talent-development#hiring#scaling#management
Explainer28:00

The Common Ingredients of High-Performing Teams

Across Dropbox, Canva, Grammarly, Miro, and Webflow, Melissa sees four recurring ingredients: clear goals plus a mission (the why), a results-oriented but team-first culture, an ownership mentality, and having fun. She warns that clear, measurable goals can accidentally pit teammates against each other, so a collaborative 'team sport' culture is essential.

  • Clear goals and knowing what success looks like, plus a mission that answers 'why'
  • Webflow example: North Star is ARR, broken into leading indicators like activation and new customers
  • Results-oriented culture must be paired with team-first collaboration ('1 + 1 = 3')
  • An ownership mentality with strong agency, not diluted accountability as you scale
  • Having fun and not taking things too seriously

“I think that's what ends up being like a situation where 1 + 1 = 3.”

Melissa Tan · 30:30
#high-performing-teams#culture#growth-teams#ownership
Explainer43:30

Her Interview Trick: Give Feedback Before the Presentation

Melissa's PM interview process runs live problem-solving at the hiring-manager screen (often pulling up the real pricing page and asking 'what would you change and why?'), then competency-focused panels, then a final presentation. The distinctive step: a prep call where she gives feedback on the draft presentation, then watches whether the candidate incorporates it. That's her biggest signal for what it's actually like to work together.

  • Live problem-solving at the manager screen weeds out the most people
  • She pulls up the real product/pricing page and asks what they'd test and why, probing 'why' repeatedly
  • A prep call lets her give feedback on the draft presentation before the final round
  • Whether they incorporate the feedback is the biggest signal of collaboration fit
  • Presentation is scheduled ~1 week out, capped (e.g., 30 slides), 30 min + 15 min Q&A, on the actual role's problem

“what is it actually going to be like to work together?”

Melissa Tan · 44:00
#hiring#interviewing#product-managers#process
Explainer50:00

The Most Common Growth Mistakes Companies Make

Melissa's list of recurring growth pitfalls: no big-picture go-to-market or pricing strategy from the start; copying other companies' best practices instead of starting from your own data and hypotheses; right-sizing experiments wrong (too small to matter, or too big with no clean hypothesis); and failing to define how growth teams work with the rest of the company so growth feels like a bolted-on layer.

  • Not being strategic early about go-to-market and pricing/packaging (revisiting pricing at scale is a huge headache)
  • Copying best practices instead of starting from your own data and customer conversations
  • Experiments too small to move the needle, or a full redo with no clean hypothesis (her Dropbox checkout redo failed for unclear reasons)
  • Not defining the 'flying formation' of how growth works with other teams, so growth feels like a layer on top

“I redid the checkout page to something that I thought was like better UX but then I changed so many different components that it was…”

Melissa Tan · 52:30
#growth#mistakes#pricing#experimentation
Explainer58:30

Your First Growth Hire Should Be a Portfolio Manager

After product-market fit, Melissa says the first growth hire is usually an acquisition person to reach the first thousands of customers at scale. Think of them like a portfolio manager: analytical, creative about finding the user, and able to test channels and identify the one or two that make up 80% of sign-ups. She argues against over-indexing on expertise, which can create false precision; hire for attributes and first-principles thinking.

  • First growth hire is usually acquisition-focused, to reach the first thousands of quality, monetizable customers
  • Treat them like a portfolio manager testing channels (they can leverage SEO/paid agencies) to find the 80/20 winners
  • Hire for attributes (analytical, creative, first-principles) over expertise
  • Too much expertise can cause false precision; paid-marketing expertise matters more later (incrementality, many campaigns)
  • Activation and pricing need attention early but not a dedicated hire; an advisor can guide an earlier-career hire

“the more it actually can lead to like false precision and then thinking they know what they're going to do.”

Melissa Tan · 1:04:00
#growth-hiring#acquisition#first-hire#founders

Story· 4

Story07:30

What Dropbox Got Right and Wrong in Its Shift to B2B

Reflecting on 2013-2017 as Dropbox scaled from ~200 people to 1,500 and a $10B IPO, Melissa names hiring (selective, first-principles thinkers) and execution as what they got right. The mistakes: starting the enterprise/sales motion too late, not clarifying the consumer-to-B2B blueprint early, and treating growth as a layer bolted on top of product rather than front-and-center.

  • Dropbox hired for first-principles thinkers plus humble, collaborative, team-oriented people
  • Recruiting was infused into the culture; everyone was trained to sell Dropbox and close talent
  • Execution matters more than best practices: their 2013 growth experiments failed until they got more user-centric and hypothesis-driven
  • They started sales/enterprise later than they should have and competitors caught up
  • Growth and revenue were treated as 'dirty words' early on ('a good product should sell itself')

“the devil's in the details and the devil's in how you execute”

Melissa Tan · 09:30

“Back in 2013 in tech, growth was kind of like this dirty word and revenue was a dirty word.”

Melissa Tan · 10:30
#dropbox#growth#b2b#hiring#product-led
Story17:00

The Feedback Conversation a Report Thanked Her For a Year Later

Two to three weeks after a new hire joined, Melissa pulled them aside to say they needed to move much faster and gave a concrete plan. The person went 'on a tear' and, a year later, thanked her for the direct conversation. Her lesson: state your intention ('I'm doing this to support you'), offer help, and keep feedback about the work, never finger-pointing.

  • She gave the hard 'we need to move a lot faster' feedback just 2-3 weeks in
  • Restate your intention and why you're having the conversation
  • Say you believe in them and offer concrete support
  • Keep feedback about the work itself, not the person: 'this is what I observed, this is the impact'

“the more direct you can be, but also saying this is my intention. My intention is to set you up for success. That goes really…”

Melissa Tan · 18:30

“as you give someone feedback, it should never sound like finger pointing or criticizing.”

Melissa Tan · 20:00
#feedback#management#leadership#coaching
Story32:00

Why She Pushed Back on Doubling the Growth Team

As Melissa left Dropbox, finance calculated each growth PM was bringing in over $1M ARR/year from experiments and logically proposed doubling the team to double ARR. She pushed back hard: doubling would fragment scope into tiny pieces (one PM owning just the checkout flow) that wouldn't be meaty enough to attract or excite great people. The lesson: ownership starts with carving out scope worth owning.

  • Finance saw each growth PM generating >$1M ARR/year and wanted to double the team
  • Melissa pushed back because doubling would slice scope too thin to be interesting
  • Carve scope by meaty problems or funnel areas (activation, monetization), not tiny surfaces
  • Ownership also means a leader taking responsibility when the team fails

“if we double the team, what is everyone on the team going to own and drive?”

Melissa Tan · 32:30
#ownership#growth-teams#scope#team-building
Story1:08:00

The First-Principles Aha Moment: Dropbox's Unconventional Sales Team

Dropbox's early sales team was full of very smart people who had never done sales (Melissa herself answered the 1-800 number and the website chat bubble). Despite the disadvantages, it drove enormous innovation and gave people deep user context that later fueled other functions. Her takeaway: smart people who've never done something can innovate precisely because they come in assuming they know nothing.

  • Dropbox hired smart people with no sales experience to do sales
  • Melissa started on the sales team, answering the 1-800 number and website chat
  • The approach produced innovative go-to-market motions and deep user context
  • That context later helped many of them (including Melissa) move into growth and other functions
  • Beginners who assume they know nothing innovate; experts who think they know the answers are limited

“if you take people that are just super smart, they've never done it before, one advantage of that is they can like innovate”

Melissa Tan · 1:09:00
#first-principles#dropbox#innovation#sales

Q&A· 2

Q&A14:30

Why People Follow Her From Company to Company

Asked what makes people follow her across companies (in some cases three times over 10 years), Melissa credits a deeply people-focused approach: caring about people, building trust, and investing in their career development. It started from paying forward the mentorship she received early in her own career.

  • She has worked with some early-Dropbox teammates multiple times over 10 years
  • Core of her leadership: deeply caring about people and building trust
  • Investing in career development and helping people figure out where they want to go
  • The approach grew out of paying forward great mentors and managers she had

“I think it just comes down to deeply caring and everything all your actions follow through from there.”

Melissa Tan · 15:30
#leadership#retention#management#mentorship
Q&A34:30

Team-First Culture When Everyone's Reviewed on Individual Impact

Contrasting with Meta's heavily impact-driven reviews that can make people hoard credit, Lenny asks how to keep a team feeling collaborative. Melissa says it comes down to the manager setting the tone: she uses her cross-team context to connect people, encourages contributions that don't feed a person's own metrics, and leads by example by helping other teams herself (like driving Webflow's enterprise pricing outside her scope).

  • Individual-impact reviews (e.g., Meta) can push people to hoard credit
  • The manager sets the tone that results matter but it's a team sport
  • She fills in context to connect teammates even when it doesn't boost their own metrics
  • Leads by example: drove Webflow pricing/packaging (even enterprise) though it wasn't her scope

“make it clear that even though results are important, it's a team sport.”

Melissa Tan · 35:30
#team-first#culture#management#collaboration

Tool· 1

Tool1:10:30

Melissa Tan's Book and Product Recommendations

In the lightning round, Melissa recommends the leadership book Leaders Eat Last (Simon Sinek) plus two non-career reads, The Untethered Soul and The Four Agreements. She also cites Radical Candor earlier (Kim Scott workshopped it at Dropbox; 'care deeply, but challenge directly'). Her favorite recently discovered product is ChatGPT.

  • Leaders Eat Last by Simon Sinek (leadership)
  • The Untethered Soul (on being present) and The Four Agreements (short, principled read)
  • Radical Candor by Kim Scott, summarized as 'care deeply, but challenge directly'
  • Favorite recently discovered product: ChatGPT

“care deeply, but challenge directly”

Melissa Tan · 42:30
#books#recommendations#tools#leadership

Takeaway· 1

Takeaway22:30

How to Find a Mentor (Never Ask 'Will You Be My Mentor?')

For people without a strong manager, Melissa advises choosing jobs with leaders who have a track record of developing people, and picking roles where your success is tied to your manager's success. On external mentors, she echoes Sheryl Sandberg and Tim Ferriss: don't formally ask someone to be your mentor. Keep it organic, reach out when you actually have a problem, and be respectful of their time.

  • Look for managers with a reputation and track record for developing people; interview them on their management philosophy
  • Pick roles where your success is tied to your manager's success (they'll invest more in you)
  • Asking 'will you be my mentor?' puts too much pressure on both sides
  • Organic relationships form strongest when you actually work together
  • You don't need a recurring cadence; reach out when you genuinely have a problem

“it's just going and reaching out when you actually have a problem. People that want to help others are are just going to if they…”

Melissa Tan · 27:00
#mentorship#career#management#advice