Problem Statement
Many job search guides fail to offer meaningful insight into landing Product Manager (PM) jobs at startups and growth-stage companies. They tend to over-index on popular interview questions, and while that’s useful to a point, they don’t teach you how to differentiate yourself in an increasingly competitive market.
If you’re a PM wondering how to break into startups and growth-stage companies from the outside, or if you’ve been trying and have struggled to gain traction, read on!
In this article, I share what I learned in my search for PM leader roles (i.e. Director / VP / Head of Product) as a candidate coming from a lengthy PM stint at a large company (8.5 years at Wells Fargo). My advice is relevant for those pursuing IC roles, e.g. Senior / Principal PM.
This isn’t a 101 on resume writing or interviewing. I assume you know the basics. What I highlight are the dynamics of the current environment and what to do and what not to do.
Table of Contents
- Everyone wants to get into Product
- Sharpening your resume
- Finding jobs worth applying for
- Preparing for your interviews
- Nailing the interview
- Negotiating an offer
Everyone wants to get into Product
Product is one of the most influential roles in driving the right customer and business outcomes. In the excellent book Inspired, Marty Cagan of Silicon Valley Product Group writes:
I’ll say right up front that [product leader] is a difficult role, and it is difficult to perform well. Those that do succeed in it make a dramatic difference for their companies. Great product leaders are highly valued and often go on to found their own companies. In fact, some of the best venture capitalists only invest in founders who have already proved themselves as great product leaders.
If you’re seeking a PM role, you’re competing against lots of highly motivated people who are or want to be in the Product game.
When job searching, you are the product, and you must convince employers that you are the strongest product/market fit for them. Approach it as you would any problem space as a savvy PM. Research your customer (i.e. the employer), sharpen your value props (i.e. your resume / LinkedIn profile), and hone your messaging (i.e. your responses to expected questions).
If you aren’t willing to put in the work, those who do will outshine you.
Sharpening your resume
Recruiters spend 7.4 seconds on average skimming a resume. It’s critical that the beginning of your resume is so compelling that they want to keep reading. Don’t expect recruiters to read through the weedy details of your resume to discern the fit; you’ve got to connect the dots for them. This is particularly true with the overwhelming volume of applicants in today’s market.
Therefore, there are 2 things a product leader should include at the beginning of a resume:
- A concise, punchy summary
- A list of specialties that matter
The more experience you have, the greater the need for a summary and list of specialties. In your specialties, include those that employers express they are looking for in the job description. E.g. hiring a team of PMs, full lifecycle product management / 0->1, leading cross-functional teams, etc. Obviously, don’t lie; you’ll get exposed at some point and you’re setting yourself up to fail.
One of the biggest barriers that applicants from large companies face is the perception that they’ll sink at a startup or growth-stage company. If your current employer is a large company, your resume has to tell a convincing narrative. You may be competing against PMs from other startups, BigTech (i.e. the FAMGA crew), or well-known disrupters (e.g. Airbnb and Lyft), so you have to make it clear that you can swim and merit consideration.
If you have experience at startups / growth-stage companies that are not well-known, make it obvious. I added “At a 15-person management consultancy” and “At this 30-person startup” in the descriptions of previous employers because interviewers at multiple companies had never heard of them.
If you have no experience at startups, focus on compelling examples of innovation or positive disruption. Here are 2 of my examples at Wells Fargo:
- I was the 1st PM in the company to launch a new customer-facing capability (secure upload) on mobile, tablet, and desktop simultaneously (in 2014) using mobile first design principles. Prior to that, we delivered desktop first then did mobile later, which as we all know now is bass ackwards
- I was on the pointy tip of the spear for Agile adoption & transformation. I was the Product Lead (commonly known as Product Owner) for the company’s 1st Agile pilot team in 2014, and two of my direct reports (Senior PMs) were the POs on early Agile adoptions after that. I was highly sought after for advice and helped shape how we practice Agile across the Digital organization (70+ scrums)
Given that I had startup experience, I chose not to emphasize the 2nd example in my resume, because they assume you know Agile. I spoke about the 1st example in some interviews. Had I lacked startup experience, I would have emphasized both in my resume as proof points that I can swim.
If you lack compelling examples of innovation or positive disruption, think about how to position yourself at your current employer to get that experience. E.g. can you get yourself staffed on that big effort to redesign / relaunch your company’s mobile app, or join a team that’s building out new payment APIs? If you have not played a PM role before, it’s often easier to transition within your existing company to a PM role than convincing a new company to hire you with no direct experience.
My job search lasted 3 months before I landed a dream job at a fintech. Over that time, I iterated heavily on my resume and authored 4 versions, and the latter versions far outperformed the former ones in terms of positive response rate. And yes, I absolutely tracked the data. Be willing to iterate on and A/B test your resume, just as you would with any product idea. You’ll know when your resume works when you get invitations for phone screens from recruiters.
For me, there was no meaningful correlation between submitting optional cover letters and getting phone screens (again, I tracked the data). Another former co-worker experienced the same. Gone are the days where a cover letter was a requirement for most employers, or that providing a cover letter signaled serious intent. Your resume is your cover letter. Obviously, if a company requires a cover letter, submit one, but if it’s optional, in my experience it’s not worth the bother.
I kept the content in my resume and my LinkedIn profile in-sync throughout my job search — some interviewers prefer reading one over the other. Look at the LinkedIn profiles of PMs to see how your peers articulate their value and experience.
Finding jobs worth applying for
It’s never been easier to find job postings. However, many people limit their search due to that convenience.
I believe there are 2 common mistakes these days:
- Using LinkedIn Jobs as your primary source of job postings
- Applying to the startups and growth-stage companies that show up in top 20 category lists
The issue with both of these approaches is that they’re lazy and obvious. It’s quite common for job postings at trendy companies on LinkedIn to have many dozens or even hundreds of applicants within a few days. If you’re applying this way, it’s like trying to get into a popular nightclub with a deep queue line — you’re a face in the crowd. I’m not saying that you shouldn’t apply to the usual suspects. Just have realistic expectations and simultaneously explore other options.
Several of the job openings that appealed to me the most were at companies that didn’t show up prominently on LinkedIn or in top 20 lists on Google, because they were on the cusp of making it or were killing it below the radar. Think of potential employers like stocks you might buy: the best opportunities often aren’t the ones everyone knows about but rather hidden gems that haven’t yet reached mainstream recognition. Such companies tend to provide fantastic growth opportunities as they scale. How do you find these gems? A terrific source are VCs: go look at their portfolio companies. I found several intriguing opportunities that way.
If you find an attractive posting on a job site, I think it’s best to apply on the company’s site directly. Why? Sometimes a posting was submitted by a recruiting firm, and you want to get your resume directly into the hands of the company’s recruiters. Another good reason to check the company’s site is that some positions may be missing on a job site, whereas a company’s site tends to be current.
During my job search, I reached out to 3 former Wells Fargo PMs for guidance:
- One landed a Sr PM position at a fintech. She advised casting a wide net between IC and leader roles. Her reasoning: at a startup you can quickly advance if you prove your worth. I saw a great example of this when I interviewed for a Director of Product role at a DevTools startup. The hiring manager was a VP of Product who had been hired as a PM and got promoted straight to VP
- One landed an L7 product leader position at Amazon. He recommended applying for IC roles for the same reason as the prior person and because roles are fluid. From his perspective, given the high number of applicants, applying without a referral is not advised. While I did have success applying without a referral, his point is spot on: if you know someone who works there, have that person submit you as a referral. It significantly increases the chance that you’ll get a phone screen
- One referred me to two P2P lenders that he’d interviewed with, so I was able to meet with the hiring teams without having to apply. Talking to him made me keenly aware I needed to brush up on emerging fintech trends and business models in that space before the interviews
There’s a lot of fluidity at small companies, so it’s more important to focus on the responsibilities of a given job posting rather than the title itself. E.g. the Director of Product opening at one place may have greater influence than the VP of Product at another. Executive recruiters pointed out to me that there is a lot of title inflation (without commensurate compensation) in Silicon Valley.
The takeaways from our experiences:
- Have an open mind about IC and leader roles
- Focus on a role’s responsibilities and sphere of influence to discern how senior it is — title alone may not tell the story
- Leverage your network as appropriate, but don’t be dependent on it
- Don’t get dejected when you’re rejected — there’s a ton of competition
- Keep refining your resume; figure out what resonates with recruiters
- Be prepared to apply to many companies; when fishing you keep casting because that’s increases the probability you’ll catch a big one
- Treat each interview not just as a job opportunity but also as a valuable learning experience
Once you start getting phone screens, you may need to throttle how many jobs you apply to, because interviewing takes time, and before you interview you should meaningfully prepare.
Preparing for your interviews
Before my phone screens with executive recruiters, I did my homework on their company & industry, thought about pertinent questions to ask, and mulled over ideas for evolving their products. I expected that any savvy candidate for PM leader roles would do the same. However, I quickly discerned from executive recruiters that some candidates show up to a phone screen without knowing much about their company. This floored me.
Here are verbatims from 2 executive recruiters who screened me:
It’s refreshing to talk to a candidate [for this VP of Product role] who was so well prepared.
It’s like you’ve been a fly on our wall! The challenges you talked about to succeed in this [Director of Platform Product Management] role are exactly the problems we’ve faced over the past year in staffing it. I’m writing an email to the hiring manager about you right now.
How did I get these kinds of responses? P-R-E-P-A-R-A-T-I-O-N. Your preparation is a huge opportunity to differentiate yourself.
As interviewers gave the introduction to their company and the role, I asked perceptive follow-on questions and shared relevant opinions on their market dynamics. When done well, this accelerates the interview to the juicy parts and pivots it to a conversation. An interview is bi-directional tire kicking, and if you wait until the latter part of an interview to ask questions, you’ll miss opportunities to get answers, glean insights, and demonstrate that you grasp the challenges they’re facing. You can only do this effectively to the extent you prepared beforehand so you show up armed with meaningful perspective.
There are plenty of easily accessible sources of information on an employer:
- The company’s site (duh): the story of the founders / mission, products, press releases, and prospectus / annual reports. The latter artifacts provide meaty details into the business model, opportunities, and risk factors for the business
- Glassdoor: the unvarnished truth from employees. People who post reviews are typically highly motivated — either very satisfied or very dissatisfied — so be discerning when evaluating their reviews
- Pitchbook / Owler / Crunchbase: company profile, size, where they are with respect to funding, competitors, etc
- Starting but not finishing their sales funnel: start the process to open an account, but as soon as you provide your email address, stop. You’ll get marketing emails over the following weeks that convey their product’s value props to customers in different ways
- LinkedIn profiles for interviewers and the organization: I gleaned so much gold by looking at the profiles of people already there. E.g. what were their backgrounds, how many people were at which levels, how fast were they promoted, etc
Research takes time but is so worth it. These days, many struggle to get phone screens or to advance deep into the interview process, so make the most of each opportunity and learn from them. Also keep an open mind; 2 of top 3 opportunities in terms of appeal to me did not stand out when I read the job postings, but after talking with interviewers I was seriously interested.
There’s more to talk about in terms of interviewing effectively and negotiating an offer, but hopefully the insights above will help you get there.
What do you think are other key tips and insights for job seekers? Please share your thoughts and experiences in a comment below.
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