Kieran Flanagan on Hiring for Growth, Building Community and Creating a Media Brand

Kieran Flanagan, a marketing leader at HubSpot, began as a computer engineer before moving into marketing. He was asked to build a product-led growth motion at the established company, drawing on groundwork he credits to Brian Balfour. He says he learned growth by doing and is drawn to what he sees as the next important challenge.

Flanagan describes a common evolution: a company first experiments with growth in a chaotic way, then establishes a central team and eventually embeds growth principles in product management. In his view the field has become more clearly defined, though the right organization depends on the company.

In a product-led model, he defines growth as acquiring, onboarding, upgrading and retaining users through models and experiments. In a sales-led business, a growth team may instead concentrate on performance marketing such as search, paid advertising or affiliates. The label can mean different things in different go-to-market motions.

An early company does not necessarily need a senior growth leader first. Flanagan has seen a single engineer work on a clearly defined metric such as retention. A leader becomes more useful when there is sufficient work and a growing team needs dedicated management.

He thinks growth principles can matter before product-market fit if they inform the product roadmap, rather than requiring a separate growth organization. As an example he cites Genius allowing users to annotate lyrics: the richer content, in his account, helped it compete in search. The example is his interpretation of the product’s growth.

Before product-market fit, Flanagan would focus on retaining a meaningful cohort of users; after fit, he proposes revenue as a combined measure of acquisition, upgrades and retention. He presents this as a practical rule, not a universal measurement for every business.

He cautions founders not to solve a later company’s problems too early. The immediate task is to build a product, listen to customers and find a use case people return to. Growth mechanisms can help, but obsessing over scale, complex onboarding or viral loops before fit often wastes resources.

HubSpot underestimated the organizational change required to move from a traditional sales-and-marketing model to product-led growth, Flanagan says. Product, engineering and customer success had to work with sales and marketing in new ways. He presents different team structures as fits for different business models.

For a marketplace whose product is central to its go-to-market, he favors a central growth team in product owning key metrics. For other product-led companies, marketing might acquire demand while a product team handles onboarding, monetization and retention. In sales-led firms, the growth function may resemble performance marketing.

His hiring process has three parts: an informal conversation about what interests the candidate, formal interviews with people who can assess experience and problem-solving, and optionally a case study. The aim is to assess fit with the company, team and particular problem, not merely a familiar résumé.

In the initial conversation he looks for a problem the candidate will enjoy and that both draws on experience and stretches them. He values the openness of a beginner’s perspective. Later, a small group can examine the case study and give a fuller view of how the candidate thinks.

For a growth case study, he suggests a hypothetical company goal and model across relevant metrics. Ask the candidate to prioritize one metric, propose a team and experiments, and explain the trade-offs. He would challenge an experiment to see whether the person can defend a well-reasoned disagreement.

A founder need not already have a growth model: the exercise can use an existing one, a hypothetical model or a model the candidate creates. Flanagan prefers supplying some data and complexity so the candidate must work through constraints rather than setting only an easy problem for themselves.

He sees founders hire growth teams without defining what they should achieve over the next 12 months. In the first year, he says, the CEO or founder must sponsor the team and explain its mission, especially when it needs to work across functions that already own parts of the product.

To scale with a company, Flanagan says a leader should identify a few inputs that really matter and build systems around them. A leader should also develop people capable of taking over existing responsibilities, freeing time for new work as the company grows.

He gives examples from HubSpot: he says the media organization had roughly 80 people at the time and describes hiring a leader with deeper media experience after the acquisition of The Hustle. He also credits another colleague with taking on demand generation. These are his descriptions of the company and team in 2022.

One of his hiring mistakes is being overly impressed by a candidate’s personal brand. Some prominent creators are excellent operators, but visibility can exceed actual experience. Stebbings adds that a prestigious employer is also not proof that a person can reproduce its growth at a much smaller startup.

Flanagan argues that an average marketer can benefit from an excellent company’s momentum, so interviewers should distinguish individual contributions from collective results. He also emphasizes that strong creators have a real and demanding skill: making material people care about.

Stebbings criticizes bland product messaging. Flanagan thinks brands often avoid distinctive points of view because a middle position feels safe. He predicts that companies will increasingly need to engage with contemporary culture and create content that speaks to their audience; this is his view of marketing’s direction.

He says HubSpot built a tribe around inbound marketing, but a once-transformational message becomes ordinary practice if it succeeds. That makes it difficult to preserve the original sense of being for or against an idea as the audience grows. His analysis comes from a HubSpot executive.

At scale, a public company has to reach a wide audience without needlessly alienating it, he says. Even so, he believes technology brands will increasingly resemble media brands, combining useful education with inspirational content. He presents that as a prediction rather than an established requirement.

The hosts discuss Elon Musk as an example of a public figure who tests what resonates and creates emotional responses. Flanagan sees this as a lesson in connecting with a particular audience, while acknowledging positive and negative reactions. His assessment is opinion rather than a measurement of all audiences.

Companies often underinvest in content, he argues: they may fund advertising heavily while paying little for articles. He suggests compensating creators well, giving them freedom and potentially sharing upside. HubSpot had launched a creator program intended to work with independent creators while allowing editorial freedom within limits.

Great content also needs distribution. Flanagan praises The Hustle team’s ability to find less-covered information, develop a distinctive angle and think about how people will see it. Simply publishing and assuming an audience will appear can leave valuable work unused.

He calls data both a benefit and a constraint for marketing. Measurement helped marketers demonstrate revenue impact, but requiring every piece of content to produce immediately attributable revenue can push teams toward the same safe, incremental choices. He says HubSpot’s acquisition of The Hustle reflected a longer-term bet on audience and brand.

Community is another term he finds inconsistently defined: one company may mean a forum where people interact, another may count an email list or social following. For him it is a group sharing beliefs and engaging meaningfully, although he acknowledges that the field lacks a settled definition.

Stebbings asks whether community can scale without losing depth. Flanagan says the answer depends partly on what is included, from events and media to small chat groups. He sees a tension between broad reach for business growth and smaller groups where people can build genuine connections and learn together.

He predicts better tools for segmenting communities and speculates that ownership incentives associated with web3 could help create broader participation. He also expects only a small number of communities to win very large returns because people can participate deeply in only a few. These are forward-looking views, not evidence of guaranteed outcomes.

He describes three potential sources of community value: personal learning, connections with peers and reputation or credentials that can open opportunities such as jobs. He thinks strong communities combine broad access with smaller groups and a way for members to receive value from their contributions.

For horizontal products, Flanagan suggests broad use and word of mouth can drive distribution, while specific vertical use cases become more important for monetization. He uses Calendly and Notion as illustrations, while acknowledging uncertainty about how much website positioning contributes to their growth.

Looking back at HubSpot, he says the company built a large educational audience and customer community, but could have done more to connect learners to one another in communities of practice. He describes courses, credentials, cohort learning and workshops as opportunities. His scale figures are company-side claims from the interview period.

Stebbings notes that community spending can be hard to tie to a clear payback period. Flanagan recommends thinking of a portfolio of short-term measurable work, long-term measurable work and long-term work that is difficult to quantify. A founder needs conviction to sustain the last category without immediate revenue attribution.

Cross-functional communication was a hard lesson for him. Flanagan says he used to see decisions as right or wrong without understanding the context faced by another team. He learned to work in the gray and recognize that product managers, engineers and marketers often approach problems in different ways.

Marketers may arrive with a list of solutions, while product and engineering want clarity on the underlying problem and room to develop a solution. He does not claim HubSpot had a neat playbook for resolving this: teams worked through friction, disagreements and rebuilding trust over time.

For new hires, HubSpot’s people team builds a 100-day onboarding plan, he says. It schedules introductions, sets expectations for the early months and checks in every two weeks. The aim is to help a person understand their role, team and path to success rather than merely demand a fixed list of achievements.

Flanagan names operations and administrative processes as a personal leadership weakness: they are necessary but not what he naturally enjoys. Angel investing has also made him appreciate how difficult it is for founders to build a successful company, rather than assume every startup grows like HubSpot.

In the quick-fire round he says email automation remains important, while he expects paid advertising and search to face pressures over time from privacy, costs and distribution changes. His forecast is that tactics often plateau or become less effective rather than abruptly disappear.

His advice for a growth leader starting a role is to stay close to customers, understand the data and advocate for the team. In remote onboarding, he says, leaders must proactively arrange introductions because the informal conversations that happen in an office are less likely to occur spontaneously.

He wants the growth discipline to become clearer about team structure, goals and alignment. He also jokes that he bought about 100 domains and once considered a calendar for remote workers to meet peers, but never built it. The hosts’ comments on a similar company’s valuation are conversational claims, not verified figures.

Asked about impressive growth strategies, Flanagan names Canva’s template and marketplace model, which he says creates a distribution engine through search. He also finds the game mechanics of the move-to-earn app STEPN interesting. These are his 2022 examples and assessments, not predictions of their future performance.