Do you start your retail career at the Gap or Abercrombie? Your marketing career in-house or a digital agency?

It doesn’t matter because you can always adjust your trajectory. 

But when you’re mid-career, finding your next tech job, each decision carries more weight. You have a finite number of career moves left. 

If you’re 40-years-old, you may plan to work 20 more years, and anticipate a change of roles every 3-4 years. That’s only 5-7 more roles left.

These roles are likely more senior as well. Each one you take means passing on 2-3 potential roles. So the opportunity cost of each mid-career decision is also more expensive.

Finally, you’re going to spend a lot of time in these final roles, physically and mentally. You want the time spent doing something meaningful, around people you enjoy. You want to make the time count.

So when you’re trying to find your next tech job in the middle of your career, have a clear plan. Not because the plan won’t change (it will) but because as Eisenhower said, “it’s the planning, not the plan.”

Even if you veer away from the output, the process of reflecting, thinking, getting feedback is invaluable.

Before taking my most recent role in tech, I spoke to over 20 people about how they navigated the middle of their careers. The people I spoke to ranged from product managers to C-suite executives. All were unique in their circumstance but shared common themes in their approach.

As common right approaches emerged, so did common wrong approaches. We’ll touch on that next.

Where people go wrong in finding their next job

The wrong approach fits into three big buckets:

People are reactive instead of proactive. They begin all the machinations of finding their next job only when they need it (testing the job market, collecting samples, interviewing, etc.) If your job search is a reaction to needing a job, time becomes the enemy. A hard deadline leads to sub-optimal decisions. When your family needs the paycheck, it becomes hard to say “no, this isn’t the right opportunity – I’ll wait for the next one.”

People optimize for vanity metrics. The two common vanity metrics are brand and salary. You join the brand name company because, you reason, it “can’t hurt” to have that ubiquitous social networking site on your resume. You perform similar mental gymnastics over salary. Taking the higher salary means “more optionality later.” There are times when you should optimize for brand or salary, but it shouldn’t be the default option.

People follow the wrong decision-making framework. People love to cite the Regret Minimization framework (I’ve done it myself).

It did come from the Mouth of Jeff Bezos, so it’s got to be right, right?

Regret Minimization is insightful at the macro-level (“should I chase this crazy idea or stick with my job?”) but you can’t use it to tackle practical tradeoffs (“should I take this job with a great manager I love or with this series B startup that seems to be a rocket ship?”)

The execution of these practical decisions is just as important as a macro decision. Bezos chose to sell books first because of strategy, not to minimize regret.

Another example: Learn vs. Earn Framework. There are many versions, but the canonical yarn comes from Mark Suster’s anecdote about an HBS-grad deciding between a COO vs. CEO role. This framework sets up a false choice between the two as if they are diametrically opposed. Similar to Regret Minimization, it’s not practical in weighing tradeoffs.

When I distilled the themes on how others found their next tech job, it boiled down to two questions: (1) Where do you see yourself in 10 years? and (2) What are you optimizing for right now?

I’ll quickly cover the first question, then spend more time on the second.

“Where do you see yourself in 10 years?”

This question can be a treacherous one. It’s hard enough to predict where you’ll be for Thanksgiving this year, never mind predicting your career a decade from now.

But when I asked Ravi Mehta (former CPO at Tiner) for career advice, it was one of the first questions he asked. Then he scoped down the question:

“In 10 years, are you an employee or CEO?”

As an employee, you’ll go down one path that involves working your way up as an executive. Therefore, it may be worth spending time at larger organizations. You’ll learn how to manage and earn buy-in on your ideas. Also, as an employee, adorning your resume with brand names carries more weight.

If you go down the CEO path, brand names typically matter less (you may be slightly more fundable but that’s becoming less and less important). More important is getting early-stage experience, which means going to smaller, less-known companies.

You don’t need your whole life mapped out but you should be able to answer this question.

I’d strongly recommend writing down your answer and keeping it front and center as you evaluate companies.

If you don’t explicitly write it down, it’s easy to get starstruck by brand and salary (see: short-term metrics, above), then post-decision justify why you took that quarter-million total comp offer from a search engine giant when you plan on starting your d2c eCommerce business next year.

With that first question answered, you can use the second set of questions to drill down further into what your next role technology job may be.

“What are you optimizing for?”

An executive shared his story about getting the offer for the head of growth role at a hot, social-audio app with a $4b valuation.

He turned it down.

When other executives inevitably told him he was crazy, he said: “I’m not optimizing for brand anymore.”

This particular executive already led growth at the ubiquitous social networking app, a social photo app, and a grocery delivery and pickup app. He already checked the “brand” box thrice over. Did adding another buzzy logo to his resume help him achieve his next goals? He didn’t think so.

Once you have a general sense of direction (“employee or CEO?”) the second question you have to answer is: “What are you optimizing for?” Levers to consider in your career:

• Stage
• Role/title
• Brand
• Company culture
• Business model
• Leadership
• Core competencies

In evaluating these levers, treat them like a constellation of metrics. One usually counterbalances against another. Depending on where you are in your career trajectory, you should be able to identify the primary lever you want to optimize for.

Let’s explore each lever.

Optimize for Stage

Optimizing for stage means joining a company based on its growth trajectory. You’re trying to maximize financial and career upside while minimizing your risk (e.g. the company failing).

Everyone I spoke to had strong, favorable opinions about optimizing for stage. Generally:

• The earlier the stage (pre-seed, seed, series A) the greater the financial upside, the greater the risk, and less defined your role.
• The later the stage (series E, series F, public) the less upside, less risk, and more role.

Obviously, it’s hard to know “when to go for it” at an early-stage startup. So much is unknown, unvalidated, and unverified. We touch on this more below in “Where is my leverage?”.

It’s worth saying: you can capture financial upside working on either side of the spectrum. To borrow from Rick Silvestrini (CMO at Verto Education), you can “collect lottery tickets” by working a bunch of startups and hope for a couple of 20x liquidity events. Or you work at a big search engine where they start you at a quarter mil total comp

Ravi Mehta thinks about stage as four large buckets:

• Startup. The company is pre-product-market-fit. Lots of risk and lots of room for growth. This stage is right for you if you thrive from building things from scratch.
• Growth. At this phase, you benefit from a rising tide. The challenge here is picking the right company; the winners are still not obvious.
• Mid-tier tech. These organizations are more mature but still don’t have defined product processes. They’re starved for the talent to help them get to the next level, which means you can still grow quickly.
• Big tech. Big tech companies are rich in talent and great places to learn thanks to defined processes and best practices. However, because there’s such a deep bench of talent, large jumps in responsibility and impact are harder to come by.

Casey Winters’s (CPO at Eventbrite) advice was to focus on stage, but “pick winners.”

“Join the smallest company that’s guaranteed to be successful. That means if you know a business (like online education) you can take more risk and join earlier. If you don’t know a business as well (like marketplaces) then join a later stage company.

“I like to tell people, ‘join a billion-dollar company, where it’s clear they’re going to win, but there’s still upside.’”

Finally, Will Wong (Partner at Andreesen Horowitz) pointed out besides the financial upside, there is also a narrative upside for optimizing for stage. The company’s narrative becomes your own, which is critical when pitching yourself to future companies.

“It’s about pitching the last role you’re in, and not much else. However, you only benefit from the halo effect if the company works out. You don’t get any credit for executing well if the company loses.”

Optimize for Role

There are three reasons to optimize for role:

1. You want to use or develop a specific skill set (e.g. SEO marketing manager so you can focus on SEO)
2. You want to grow into a specific role
3. You want a specific title (e.g. senior manager to director or head of your department)

Matt Greenberg (CTO at Reforge) summarized the first one:

“Optimize for role when you’re developing a functional skill set.”

If you want to use or develop a skill set, go where there’s a lot of support around the role and people to help guide you. This means finding a company with enough established processes around day-to-day tasks and you have peers to learn from, e.g. series D and later.

How Casey Winters put it:

“I don’t like going too early-stage if you’re building a functional skill set. If you’re trying to build skills and credibility, go where you know it’s going to work out.”

If you’re early in your career and know there’s a specific role you want to grow into (#2), you can target “entry” level roles at companies where there’s a propensity to promote within. HubSpot is a great example of this, where many product specialists are eventually groomed to become product managers.

Finally, you can optimize for role if you’re targeting a specific title (#3). Perhaps you’re a senior PM looking to jump to director, or a VP ready to jump to c-suite. One path that enables this jump is moving from a larger, more established organization to a smaller, talent-hungry organization.

When optimizing for role, it’s easy to over-optimize. You want to see the forest for the trees. You don’t want to land the perfect role at the wrong company (wrong stage, wrong culture, wrong business model).

For my most recent career move, I wanted to develop a functional skillset (growth and product management). I wanted to focus on getting better at one thing, surrounded by PMs who could help. The title was also important; for someone like me who’s bounced around across roles and industries, I wanted to consolidate my narrative in growth, in the tech industry, for this chapter of my career.

Optimize for Brand

Having brand-name companies on a website where people voluntarily post their resumes[efn_note]I lifted this directly Anna Weiner’s Uncanny Valley I laughed out loud when I read it[/efn_note] can open many doors.

These marquis names can set you up when you’re a CEO looking for funding. They communicate to recruiters, hiring managers, and future colleagues that you’ve worked on problems of a certain scale. It also communicates the type of culture (product-focused? Design focused? etc.) you’ve been steeped in for the last few years.

Having brand names will almost never hurt future prospects, but “bigger brand is better” would be an oversimplification. The wrong way to think about brand is asking “what’s the biggest brand name I can land?” The right way is:

• Where do I see myself in 10 years? (see above)
• Who is my audience in 10 years?
• What brands speak to that audience?

Crystal Widjaja (CPO at Kumu) explained when she picked her earlier roles, she avoided larger companies with bigger brand names.

“I wouldn’t focus on these companies because there wouldn’t be interesting opportunities for someone like me. They’d always have someone who’d been there longer who can do the interesting work. I asked myself, ‘Who do I want to impress?’ I want to impress start-ups and VCs. That means I don’t need certain brand name companies on my resume.”

Finally, Casey Winters added the brand might open certain doors, but brand alone won’t get you through them.

“The people who are hiring and worth being hired by will understand the differences. For me, it’s a holistic combination of all these pieces. You have to understand the relationship between brand, role, company stage, and what that all looks like on paper.”

Stage, role, and brand are the big three levers worth thinking about when it comes thinking about your next job. There are two additional levers, that play a smaller role in the calculus: company culture and your personal leverage.

Company culture

Company culture is the formal and informal rules around “how things are done here.” Let’s take two elements of culture as given:

• You want a non-toxic environment
• You want to do your job and sleep well at night

Then there are two less obvious factors to consider:

1. How entrepreneurial is the company? 

If you know where you want to be in 10 years (see above) this can influence how you evaluate company culture. Some companies have more “entrepreneurial DNA” and their people become future CEOs. Early PayPal famously gave birth to the PayPal mafia, and early HubSpot is another example.

In an attempt to create tomorrow’s mafias, there are venture capital firms that only fund startups created by alumni of specific companies like Uber, Airbnb, and Lattice.

2. Who sits on the Iron Throne? 

More specifically, “what function has the most influence on the success of the company?” If you want resources and impact, you want to sit at the center of gravity.

This again is a function of the company’s DNA. Uber’s success comes from engineering (how they algorithmically optimize supply and demand) and their operations team (“think local to expand global” playbook). Google is an engineering-driven org, while Bumble is marketing-driven. Meanwhile, at Disney, everything starts with the IP, and so content is king.

What about product-driven organizations? Ravi Mehta says a litmus test for a product-driven org is “same supply, better experience.” Superhuman (email), Slack (workplace communication), and Spotify (music). Others have been working on these spaces for years, but these companies won because they 10x’ed the experience.

Where is my leverage? 

I’ve heard this vector framed in different ways.

Matt Greenberg framed it as “what is your superpower?” Superpowers can be driven by skill sets, but many times it’s experience. For example, after Credit Karma, Matt’s superpower was a deep understanding of the fintech space.

Casey Winter’s advice about “joining the smallest company that’s guaranteed to be successful” is directly tied to your leverage. Based on your leverage, you may have an understanding of what’s actually going to work.

For example, because he had a strong understanding of marketplaces, Grubhub seemed like a no-brainer to him when it was still relatively nascent in the market.

If you worked at a company like Peloton where you understand the subscription and hardware model, you’re going to have a natural advantage over others joining a company like Tonal, Tempo, Whoop.

Depending on where your leverage is, that might mean in certain industries or business models you can join a 200 person startup, whereas for others, you should go someplace more established.

How to put these levers to use? 

First, spend the time to gather insights from research and exerts through informational interviewing and backdoor references. Then, use these levers as opportunities and challenges to think about when considering your next career move.

It’s not a strict framework or rubric you complete and spits out your dream job. If you’re the type that finds rubrics helpful, I recommend the template Adam Grenier (former VP Product & Marketing at Lambda School) created.

Understanding the levers should give you ideas and directions of how to gauge and measure companies. For example, given my goals and where I see myself in 10 years, I immediately took out most public companies from my list (e.g. Disney, Netflix, Facebook).

If you found this helpful or have any questions, let me know on Twitter!

Many thanks to all the people who’ve helped me in my career throughout the years, and in particular, Ravi Mehta, Rick Silvestrini, Crystal Widjaja, Will Wong, Casey Winters, and Matt Greenberg. Lastly, thanks to Susan Su for always helping to connect the dots.