When to Hire?

Product-Market Fit. Prior to achieving product-market fit, a startup may pivot and shift its strategy in dramatic ways. A founder should wait until the startup’s strategy has “settled down” before hiring a product leader.  At that point, skill requirements for the product leader will be more clearly defined, making it easier to identify the best candidate for the job. 

Span of Control. Another timing consideration relates to how many PMs should report to the new product leader upon their arrival. There are tradeoffs with bringing onboard the new product leader earlier, when the startup has very few PMs. On the downside, with a small span of control, the product leader may be underutilized—a waste of talent and capital, unless they assume direct PM responsibility for a portion of the product themselves. On the upside, if they inherit fewer PMs when they arrive, the new product leader has more leeway to shape the product team through new hires. Also, having a smaller and more junior set of incumbent PMs reduces the likelihood of jealous discontent among more senior PMs who might think they are qualified to serve as product leader and should have been promoted. 

Founder/CEO Readiness. When to hire a product leader hinges crucially on the founder/CEO’s readiness to share responsibility for crafting product strategy. Being overruled by the CEO can seriously undermine a product leader, because it shows colleagues throughout the organization that they can bypass the product leader and lobby the founder/CEO directly to gain support for initiatives they wish to pursue.

In a blog post, Casey Winters, Eventbrite’s CPO, says that mismatched expectations about the product leader’s role in crafting product strategy often stem from the recruiting conversations, when the CEO and candidate have exciting “jam sessions” about product vision, and the candidate mistakenly assumes that such collaboration will continue if they are hired. Winters recommends that both sides explicitly discuss the CEO’s willingness to share responsibility for product strategy.

Sam Clemens, co-founder/co-CEO of Reprise, suggests that the optimal timing for hiring a first product leader will vary with the central focus of the founder who has been guiding product development. Clemens notes that a sales-focused founder will have less natural overlap with product teams, and may find the need for frequent product meetings to be too burdensome once the startup’s PM headcount exceeds two or three. By contrast, a product-focused founder can manage many more PMs before they feel a need for a new product leader to serve as a span breaker.

Andrey Khusid, founder/CEO of Miro, provides an example of this. Khusid served as Miro’s product leader until the headcount in Miro’s product function (including PMs and designers) reached 15 to 20. At that point, travel demands and other responsibilities of the CEO role left Khusid unable to spend enough time with the product team, and he appointed an insider to lead the function.

a16z partner Ben Horowitz sees the ongoing involvement in product development of a product-focused CEO as key to startup success. As he notes in his essay, Why Founders Fail: The Product CEO Paradox, “The only thing that will wreck a company faster than the product CEO being highly engaged in the product is the product CEO disengaging from the product.”

Who to Hire?

Insider or Outsider? If a qualified candidate is available internally, does it make sense to promote them, or is an outside search the way to go?

Maggie Crowley, VP-Product at Charlie Health, points out some tradeoffs with hiring an insider. The upside: an insider will know the venture’s product; will have relationships with colleagues -- and ideally, their trust; and will understand the preferences of the founder/CEO. Importantly, such a promotion creates a culture where people know they can move up within the organization, so they aren’t forced to look externally for professional growth opportunities.

The potential downside: the CEO and senior managers in other functions may still view the newly promoted product leader as an individual contributor, rather than a member of senior management.

Skill Fit. Whether the startup appoints an insider or hires an outsider, it’s important for both the CEO and the candidate to gauge the fit between the venture’s product development priorities and the candidate’s abilities and experience. Casey Winters notes that ventures face different challenges, and it’s important that a new product leader have the know-how to address them. Poor fit between the venture’s strategic imperatives and the product leader’s capabilities boosts their failure odds.  Examples of priorities that require different abilities include:

• Re-architecting technical infrastructure to ensure scalability
• Introducing product management processes
• Refining and adding features to the core product
• Accelerating growth of the core product’s user base
• Launching additional products

How to Get Started?

A new product leader hired from the outside faces the daunting task of evaluating the venture’s product strategy; diagnosing the strengths and weaknesses of the product function; and formulating and prioritizing action plans to address problems and target new opportunities.  Ideally, they should do all this quickly. The goal: figure out whether the task ahead is a quick new paint job or a full remodeling project.

PMs’ Abilities. A key first step for the new product leader is gauging the ability of the PMs they have inherited and identifying any obvious gaps that need to be filled by outside hires. Jared Smith, co-founder of Qualtrics, encourages product leaders to determine whether they have the right mix of “builders” and “architects” in the PM role. He notes that tech products are multi-dimensional, which requires system-level thinking—a strength of great architects. Smith gives the example of time as one dimension, and asserts that few PMs possess the ability to craft product strategies that balance tradeoffs across the past (e.g., customers using old versions who may have their experience ruined by something new), present (the current version), and future (the long-term product roadmap). Smith notes that anyone who has worked on a product for less than one year has probably not experienced issues related to a full range of past, present, and future issues. The implication: to get a multi-dimensional PM, emphasize job tenure and product lifecycle experience when recruiting.

Founder’s Blind Spots. Sam Clemens posits that the nature of challenges confronting a new product leader will depend in large part on whether they will be working with a sales- or product-focused founder. Clemens notes that a sales-focused founder, when serving as product leader, will tend to prioritize features demanded by the venture’s sales reps. In developing these features, they will pay less attention to consistency in visual design; architectural coherence (e.g., opportunities for database sharing across features); and UX continuity. By contrast, a product-focused founder has probably spent less time listening to requests from the sales and marketing teams, and may have put too much emphasis on features that lack sales appeal.

Technical Debt. According to Clemens, a new product leader must also understand the amount and type of technical debt that the organization has accrued, and formulate a plan for paying down the debt over time. We’ll focus another essay in this series on how to manage technical debt, but in brief, Clemens suggests as first steps reviewing the bug backlog and checking to see if features have been built with different programming languages. The goal: determine quickly how much of the code base needs to be refactored, and the urgency of the fixes. Clemens warns that allocating too much engineering time to paying down debt upon arrival can be a risky move for a new product leader, because they won’t show enough progress on new features requested by other functions.

The Dominant Function. Along those lines, the new product leader will need to understand the role of other functions in shaping product strategy. Most startups have a dominant function, and if a startup is not “product-led,” its product leader and PMs must adapt to the dominant function’s preferences and priorities. Clemens notes that engineering-driven companies may not recognize the full range of success factors for PMs, who must at times use intuition. Engineers prefer to use formulas when prioritizing tasks, and therefore will be more comfortable with what Dropbox CEO Drew Houston calls a “librarian” PM, who’ll be inclined to quantify a new feature’s benefits and costs. By contrast, according to Clemens, a “poet” PM in Houston’s typology—one who relies upon intuition when developing a product vision— is more likely to face organ rejection in dealing with Engineering. As a consequence, in an engineering-driven startup with too many librarian PMs, non-obvious things may never get built and the venture’s product may lapse into mediocrity over the long term. The implication: in an engineering-driven startup, you want PMs who have both librarian and poet DNA.

You should move at two speeds, with urgency and with patience.

Product “Operating System.” Prior to the arrival of a new product leader, many startups employ a “lightweight” approach to managing the product function. The new leader must decide whether and when to introduce more systems, processes and policies, and in doing so must determine how much structure is too much—or too little—at the current stage of the startup’s evolution. Many product leaders describe the approach they use to manage the product function as their “operating system” or “playbook.”  We’ll focus a future essay on this topic, but in brief, some elements of a product management OS include how to organize the PMs (e.g., by feature, customer segment, conversion funnel stage, etc.); the cadence of product planning meetings; how to run product reviews; how to manage the product roadmap; what flavor of agile to use; sprint planning; the optimal number of engineers and designers per PM; whether and how to use product principles; whether and how to use a product council; and so forth.

The new product leader must decide whether to: 1) retain any aspects of the product operating system that were in place upon their arrival; and 2) import operating system elements that they have used successfully in past jobs. If such past practices are well suited for the current situation, there can be advantages to leveraging familiar systems; this allows the product leader to focus on other priorities. As head of product at Alphabet’s Sidewalk Labs, Prem Ramaswami had this experience. When new to the role, Prem employed product operating system elements from Google, where he’d previously worked. The practices worked well, because several of Prem’s first PM hires also came from Google.

The new product leader must also decide how much structure to introduce to a product team that probably is accustomed to a founder’s fluid management style. Miro’s Andrey Khusid witnessed this after he hired an outsider as CPO, who introduced product operations discipline and also streamlined several processes, for example, reducing the number of attendees at product reviews. Khusid noted, “Operations is not my strong suit, but I supported the new CPO’s moves, because I’d seen a big payoff from similar efforts to introduce more structure to Marketing.” 

Performance Expectations. Our interviewees agreed that setting high performance expectations from the outset is important for a new product leader, and shared a range of views about what to emphasize:

• Adam Nash cautioned that if a product leader sets the performance bar too low for PMs, they can set the PMs up for failure, because they deliver against low expectations but they don’t dazzle.
• Prem Ramaswami, reflecting on lessons he learned as a new product leader, noted that key success factors for a product leader are not the same as those for a PM. Ramaswami reflected that a product leader is foremost a people manager, and must allow PMs to fail and learn from that experience. Ramaswami added that an important lesson for a new product leader was how to kill projects that aren’t meeting their potential. He said, “When we conclude that we can’t add five people to a new product concept, we should shut it down.” 
• Reflecting on performance expectations, Jared Smith emphasized the power of critique in improving a product. He founded Qualtrics with his brother, and recalled that the two of them battled constantly over product strategy—“beyond the point where others would simply submit.” Smith said that they got far better ideas through intense debate, and that he now pushes his product teams to work this way. Smith added, “Being a brilliant asshole may be the only way to get this done. You have to be willing to say, ‘It’s not good enough, go again.’ A founder can be a brilliant asshole and not get fired. But in this mode, a hired product leader will eventually elicit a rear guard reaction.”
• Tripadvisor founder/CEO Steve Kaufer said he encourages product leaders to understand their boss’s priorities and present proposals in those terms—and with specific performance thresholds, for example, “we fail if usage is less than X.” That way, he says, senior leaders can look at the product leader’s goals and say, “Achieving that doesn’t excite me, so don’t proceed.” Kaufer explains that product leaders frequently do not push hard enough for this level of specificity in measuring performance because “they want to give teams a shot without seeming to micromanage them.”
• Andrey Khusid was impressed with how the CPO that Miro hired instilled a strong sense of urgency in the product team. Khusid said he previously had been ambivalent about doing this, because he “wanted to create a more inclusive, balanced culture and avoid the Silicon Valley meat grinder culture that results in turnover after 12 to 18 months” However, as Miro confronts the prospect of more competition from tech giants, Khusid is convinced that the sense of urgency imbued by the CPO makes sense, because “Miro will win or lose based on moves we make over the next 12 to 24 months.”

On the topic of urgency, Prem Ramaswami shared advice he got from Dan Doctoroff, Sidewalk Labs’ CEO, that seems like good guidance for any new product leader: “You should move at two speeds, with urgency and with patience. Get things done, but with attention to vision.” In other words, long term vision, short term execution.
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Ultimately, responsibility for the incoming PM leader's success resides with the founder/CEO.

The quickest and single biggest reason for an incoming product leader’s failure is a loss of faith from the broader organization that leads managers to bypass the product leader. This is more likely to happen when a founder/CEOs permits and even encourages such bypassing, due to their own lack of trust in the product leader’s judgment and capabilities and/or their own inability to “let go.” This can lead to a revolving door of product leaders, and with it, schizophrenic shifts in product strategy. Product leader churn will eventually hamper the founder/CEO’s ability to run the company.

A crucial factor in the incoming product leader's success is the degree of synchronicity s/he has with the founder/CEO who led the product function before her arrival. Their product visions, strategies or even execution techniques don’t need to match perfectly, but they should be in constant communication about the differences of opinion and decide, a priori, on a unified approach so that there is no dissonance within the broader organization. 

Reid Hoffman did this exceedingly well when he brought in Deep to lead LinkedIn’s product organization. The two of them would spend a few hours every week discussing, debating and arriving at a joint view on product strategy. Reid was also great about couching his views as opinions, leaving the final decision to Deep. This is true empowerment and was critical to Deep’s success at LinkedIn.