Caring Deeply, Measuring Clearly: Melissa Tan on Building High-Performing Growth Teams

Melissa Tan tells Lenny that she is leaving Webflow after about two and a half years building its growth team and returning to full-time advising. Before Webflow she advised companies such as Canva, Grammarly, and Miro, and she says her passion is working with earlier-stage companies after product-market fit to help them scale growth. She plans to focus on go-to-market strategy, product-led versus sales motions, pricing and packaging, and funnel optimization across activation, monetization, and retention. Listeners can reach her on LinkedIn.

Lenny asks Melissa to reflect on Dropbox, where she worked from 2013 to 2017 as the company grew from roughly 200 people and a $1 billion valuation to about 1,500 people and a $10 billion valuation at IPO. She says Dropbox got several things right, starting with selective hiring for first-principles thinkers who were also humble, collaborative, and team-oriented. That combination fueled innovations in freemium, product-led growth, and a high-velocity sales motion. Dropbox also infused recruiting into the culture: everyone was trained to interview and to sell both Dropbox and the roles they were hiring for.

Melissa points to execution as another strength, but with a caveat: early growth experiments failed because the team followed best practices that did not fit Dropbox rather than starting from user-centric hypotheses. When the team came back and executed differently, the details made the difference. She also cites focus as a lesson: Dropbox had consumer and B2B businesses but could have clarified earlier how the two journeys fit together. Starting sales and enterprise later than it should have let competitors catch up.

The final lesson is company-wide engagement in go-to-market, growth, and revenue. In 2013, Melissa says, growth and revenue were still treated as dirty words in tech, and Dropbox assumed a good product should sell itself. The self-serve business slowed before the company started a growth team, and growth then felt like a layer on top of product rather than being front and center from the start. At Webflow, she and Webflow's product leader have been intentional about collaboration between product and growth.

Melissa says most companies lean either sales-heavy or product-led at first, and a common path is to start product-led. Product-led is a good fit when onboarding is intuitive, the learning curve is low enough that users do not need a human to onboard them, and the product has a viral component. Dropbox, Miro, and Figma are examples she cites of products with product-led DNA. Starting product-led also generates scale and signal about what resonates with users.

As a product-led company grows, larger self-serve customers often ask for enterprise features such as SSO and stronger security. Those requests become a roadmap for the enterprise motion, which is why many companies start product-led and then move into enterprise sales. The reverse path also exists: some products are naturally sold to legal, finance, or another key stakeholder, and later the company tries to simplify onboarding and reach end users at scale. In both cases, Melissa says the key is to know where you start and then invest deliberately in the next motion.

Melissa emphasizes knowing how the whole picture fits together, especially for companies with both consumer and B2B businesses. The earlier the company can define the paths and journeys between those audiences, the more seamless the experience is for users. That was a gap she saw at Dropbox, where the consumer and B2B motions were not fully connected from the beginning.

Lenny notes that Melissa has a reputation for bringing people with her from company to company, and she says she has worked with some early Dropbox teammates two or three times over a decade. She attributes that loyalty to a people-focused approach: caring deeply, building trust, investing in career development, and helping people figure out where they want to go. She frames it as paying forward the mentors and managers who helped her early in her career.

Melissa rejects the idea that caring about people and driving impact are mutually exclusive. On a growth team, she says, almost everything is measurable, and people appreciate knowing what success looks like and how they will be measured. She creates a results-oriented culture with clear team goals, individual levers, and individual success measures, while her role is to support career growth, help people hit goals, and give feedback along the way.

She offers an example from a new hire who seemed to be moving too slowly a few weeks in. Melissa pulled the person aside and said the team needed to move faster, defined the deadline, and proposed a roadmap, problem list, hypotheses, and success measures. She also made clear that the intention was to set the person up for success and offered to help. The person later said the direct conversation was a turning point and was grateful for it.

Melissa says the conversation worked because she restated her intention, expressed belief in the person, offered support, and kept the feedback about observed behavior and impact rather than personal criticism. She recommends naming what she observed, the impact it had, and a different way to approach the work. That is how direct feedback can feel like care rather than finger-pointing.

Melissa's commitment to developing people is personal: she says the transition from school to work was hard for her because success became ambiguous, and mentors such as Oliver “OJ” Jay and GC Laney at Dropbox invested in her. She also believes internal development makes scaling smoother because people build institutional knowledge and the kind of user context that founders are often credited with. Early employees can develop that same intuition, so growing people internally de-risks the transition compared with bringing in outsiders.

For people who lack a strong manager, Melissa advises choosing roles based on the manager's track record of developing people. Candidates should ask how the manager thinks about managing and developing talent and how they think about the career path for the role. If the manager has not thought about it or does not ask what matters to the candidate, that is a signal. She also suggests looking for roles where your success will be tied to your manager's success, because that creates more attention and time together.

Melissa says mentorship does not have to come from a direct manager. People can proactively ask someone at the company for advice or a recurring sync, and external advisors can also become mentors organically. She cautions against asking someone to “be my mentor” too early, citing Sheryl Sandberg's Lean In; the request can feel like pressure. Instead, reach out with a real problem, ask for advice, and let the relationship grow if it is useful.

When interviewing a manager, Melissa would ask directly how they think about managing and developing people and how they think about the career path for the role. She would also ask other people on the panel, especially people the manager manages, what the manager is like. For external mentors, she recommends being respectful of time and reaching out when there is something specific to discuss rather than forcing a cadence.

Melissa has worked with Typeform, Canva, Grammarly, Miro, Dropbox, and Webflow, and she sees common ingredients in high-performing teams. The first is clear goals: people need to know what success looks like, especially on growth teams measured by quarterly and annual metrics. The second is a mission that explains why the work matters; at Webflow the growth team's North Star is ARR, broken into leading indicators such as activation and customer counts, while the mission is to build delightful user experiences. Monetization is a signal that users find the product valuable, especially when they keep paying and retain.

Culture is the third ingredient, and Melissa describes the culture she tries to set as results-oriented, team-first, ownership-minded, and fun. A results-oriented team can become competitive, so she explicitly encourages people to help each other, share learnings, and avoid local optimization. She wants the team to feel like owners with agency, especially as a company scales and ownership can feel diluted. She also believes fun matters, particularly in high-pressure environments.

To create ownership, Melissa starts by carving out scope that each person can run independently and is excited to own. At Dropbox, finance calculated that each growth PM was bringing in more than $1 million in ARR per year and suggested doubling the team, but Melissa pushed back. She asked what each new person would own and worried that splitting the work into tiny pieces like the checkout flow would not attract strong people. She prefers splitting growth by meaty problems or funnel areas such as activation and monetization.

Melissa also infuses an owner mentality by teaching people not to feel disempowered when they are blocked by another team, but to exhaust the options they control. As a leader, she models that behavior and takes responsibility when things go wrong on her team. On team-first culture, she says the manager sets the tone by sharing context, encouraging people to contribute outside their direct goals, and leading by example. She points to her own work driving pricing and packaging at Webflow, including enterprise pricing, even though she oversaw self-serve. She also cautions that helpful people can take on too much; she recommends time-boxing extra work and watching for responsibilities that start to drop.

Melissa thinks about developing talent across the lifecycle of the relationship. It starts with hiring for mutual fit and a growth mindset, then ramps into clear expectations for the first 90 days, connections to the right people, and early wins. She might suggest a presentation for visibility or point people to low-hanging fruit—or “rotting fruit”—that can build momentum. Later, she gives feedback along the way and helps people get visibility, including through short Loom videos shared with leaders.

Melissa connects this approach to Radical Candor, the book by Kim Scott, who was at Dropbox briefly and workshopped the material with the team before publishing it. The phrase she remembers is “care deeply, challenge directly,” and she tries to infuse that into her leadership. She also sees the manager relationship as lifelong: she stays in touch with former reports, helps with career advice, and says she has learned a lot from the people she managed.

When hiring PMs, Melissa looks for the expected communication and stakeholder skills, but she leans hardest on first-principles thinking and a growth mindset. In interviews she uses live problem-solving, asking how a candidate would approach a real problem and then digging into why. She might ask a pricing candidate to pull up Webflow's pricing page and say what they would change, a trick she learned at Dropbox. She also tests how candidates take feedback, sometimes by giving feedback during the process.

Her process typically starts with a hiring manager screen that includes live problem-solving, which she says weeds out the most people. The next round has more team members testing different competencies, and the final round includes a presentation and deeper conversations. The presentation is based on a real company problem rather than past work, because it tests how much context the candidate picked up and whether they would like the work. She schedules it about a week ahead, caps it around 30 slides, and runs it as 30 minutes of presentation plus 15 minutes of Q&A. Before the presentation, she holds a prep call, shares feedback on the draft, and watches whether the candidate incorporates it; that collaboration is one of her strongest signals.

Melissa says a common pitfall is starting growth without a big-picture go-to-market plan and a view on pricing and packaging. At Dropbox, the company found successful motions haphazardly—freemium, then a teams product—without a blueprint for how consumer and B2B fit together. She also sees companies that delay pricing decisions until they have massive scale, then face painful questions about grandfathering legacy customers and migrating them to new pricing. She wrote about this for the YC blog with Abby Kuzminov, who was on her team at Dropbox.

Another mistake is copying growth tactics from other companies without starting from your own data, customers, and hypotheses. Teams sometimes run experiments that are too small to move the needle because they heard a tactic worked at a company like Dropbox, where a 0.5% conversion improvement matters; an early-stage company may need to think bigger. The opposite mistake is changing too much at once, as Melissa did when she redesigned a checkout page and could not tell why it failed. She recommends distilling changes to a hypothesis and right-sizing the experiment.

Melissa uses the term “flying formation” for how teams work together across growth, product, and marketing. Part of it is a DACI: a driver runs the project, an accountable person is the final decision maker, contributors do the work, and informed people need updates but are not directly involved. She also includes operating rhythms, such as weekly metric reviews and quarterly planning. At Webflow, the team wrote a flying-formation doc saying product growth owns metrics downstream of sign-ups, growth marketing owns sign-ups and CAC goals, and the groups review metrics together.

On whether product growth should own revenue, Melissa says it depends on the company and what product growth is driving. In the companies she has worked with and advised, product growth usually owns revenue, but she has seen marketing own it when growth is more top-of-funnel and finance own it early, as at Canva. At Dropbox, the team moved from marketing to the revenue org with sales and finally into product because so much revenue came from product growth. For the first growth hire after product-market fit, she recommends an analytical, creative portfolio manager focused on acquisition, not necessarily a narrow channel expert. Activation and pricing/packaging matter early, but she does not think they need dedicated hires; activation can start with five user-testing sessions, and pricing should be thought through from the start.

Melissa says the first growth hire should be chosen for attributes more than narrow expertise. She wants someone analytical, creative about finding users, and able to manage acquisition like a portfolio, testing channels and using agencies where useful. Deep expertise can create false precision and make someone think they already know the answer; paid-marketing expertise matters more later, when incrementality and campaign management become central. Product growth hires typically come even later, after the company has product managers in place.

On advisors, Melissa would bring one in when the team has a knowledge gap. She recommends being explicit about goals and what kind of help is wanted, because advisor arrangements vary from monthly calls to weekly calls and joining team meetings. She prefers starting with a shorter engagement, such as a quarter, and treating it as try-before-you-buy. If the advisor is not adding value, it is fine to part ways.

Melissa defines first-principles thinking as creating your own framework from context rather than applying a set formula. It means knowing what questions to ask, forming a mental model, evolving it, and recognizing when it is not working. She is known for asking many questions, not to show off but to make sure the team is solving the right problem and still doing the right thing when new information appears. Her aha moment came at Dropbox, where the initial sales team included many smart people who had never done sales. There were disadvantages, and she thinks a mix with some experienced salespeople might have helped, but the unconventional team produced innovative go-to-market motions and many members moved into other functions with deep user context. She also started on sales answering the 1-800 number and website chat, and she learned that people who say “I don't know anything, let me figure this out” can innovate more than people who think they already know the answers.

In the lightning round, Melissa recommends Leaders Eat Last, The Untethered Soul, and The Four Agreements; her favorite recent show is Winning Time, about the 1980s Lakers. Her favorite interview signal is the prep call before the candidate presentation, and her favorite recent product is ChatGPT. A small process change with big impact was introducing a DACI, and her Webflow tips are to use Webflow University videos alongside the designer and the Figma-to-Webflow plugin. She can be found on LinkedIn and on Twitter at MelissaMTan.