DO NOT join a Series A startup if . . .
Yet another Top 10 list. You're welcome :)
I joined my current company, a Series A startup, 6 months ago this week! Rewinding a little over two years before that . . .
I joined my previous employer, a publicly traded SaaS company of ~1,700 employees in 2020. The acquisition by private equity was leaked to the press the night before my official start date. It was a shock to the system for sure. When your company is acquired, all senior and executive leaders (and most employees) instinctively know they’re now walking around with two things above their heads: a dollar amount and a ticking time bomb. This isn’t to vilify PE; it’s well-known that this is what happens. I had a double-whammy when my hiring executive left the company a few months after I joined his team.
I wasn’t surprised by his departure given that my whole career, I’ve reported to the same person for 6-12 months (average = 7.68 months) before they leave or get fired or I get promoted or leave.
When they are about to leave voluntarily or involuntarily, I now have a bear-like sense about it. (Did you think I was going to say “bloodhound-like”? Turns out, bears have an even greater sense of smell than bloodhounds; 2,100 times more powerful than humans. That’s facts. Speaking of bears, have you seen The Bear on Hulu? If the answer is ‘No,’ stop reading right now. Stop. No really. Stop and start watching the show. Are you still reading? Okay, fine. But after this.)
My supervisory circus has resulted in 25 title changes and 31 manager changes in 20 years. That’s facts, too.
But it works for me because I’m a variety over certainty person. (Also, it’s been a fascinating long-term case study in management behavior. I’ve watched leaders self-implode, stage a successful coup, survive long enough to become the scapegoat for their boss’s failings, get fired for sexual harassment or worse, burn out or—possibly the most painful of all—die a slow corporate death of complacency and under-performance.)
Craving variety is one of the reasons why joining a Series A or B company was near the top of my “get out before the bomb goes off” list.
I almost made it, too. In one of the most painful months I’ve experienced professionally, I had a job offer rescinded and two days later, my company did a 20% cut two weeks before Christmas. The timing on this has to be one of the most inhumane ways ever to rid yourself of 400 walking dollar signs, I mean, people. Layoffs have been all the rage lately in tech and there is still blood in the water.
Within 48 hours, I was recruited by my current company and so began my journey with an incredible Series A startup.
(More on this later, but I don’t want to give the impression that I only spent two evenings kinda bummed about being unemployed for the holidays and then miraculously everything was all better. Always Be Interviewing, especially once your company is acquired!
If you’re not currently in tech, I might recommend waiting to dip your toe in the water. (Think Meg 2.) If you are in tech and wondering if a swim in Series A is for you, read this first.
Top 10 reasons you should NOT join a Series A
#1 You need certainty and control and struggle with change.
Don’t worry too much about this one. (I’m easing you in.)
Here are the only things likely to change on a regular basis at a startup:
your job description, your title, the company’s priorities, your org’s priorities, your team’s priorities, your priorities this week, your priorities today, your priorities right now, your priorities like seriously right this second, performance measurements, incentives and bonus compensation structure, processes, people you work with, how important diversity is, promotion potential, budgets, headcount hiring, decisions, plans, roadmaps, goals, KPIs/metrics, political landscape, the flow of the office grapevines, rules of engagement, perks and benefits, reporting structure, remote work policy, level of transparency, rhythm of the business ceremonies and cadences, inside jokes you at one point thought you understood and now don’t. . . .
You can control almost everything else.
#2 You feel most valued when you are highly specialized in your role, not a generalist.
“A jack of all trades is a master of none, but often times better than a master of one,” the original saying goes. I prefer the concept of being a proud “multipotentialite,” the more sophisticated (and non-gendered) cousin to “jack of all trades.” If you don’t want to be the Caps for Sale guy (back to gendered again), don’t join a Series A.
When you’re hiring at a startup, you’re looking for people with 1) the potential and humility to grow quickly and 2) a little bit of this and a little bit of that skillset and experience. Specialists have their place but the most highly valued team members initially are ones that can play multiple positions on the field. (WOW. That was FOUR metaphoric / allegoric references for ONE thing. How meta is that?! I’m not even sure which sport the last one is about.)
The corollary to this one is “Don’t join a Series A if you’re not a person who naturally looks up and out from your world and asks, ‘How can I help? What more can I do?’” There is always so much to do at a startup. Pick up a shovel and start digging and then go give your neighbor a break from digging. (That’s FIVE!)
#3 You hate getting deeply personal with co-workers.
Vulnerability is the lifeblood of a startup’s culture. Especially one that’s local and has few if any remote employees. Here’s why:
Dunbar’s number(s). You can remember the names and some relevant personal details of up to 100-250 people. So when you pass the same people in the hall and in the lunchroom every day, chitchat or work-related banter can easily turn therapeutic and cathartic. Great example of this recently was a “quick chat” a co-worker wanted to have about the Barbie movie (because he knows I’m obsessed with it and because he LOVED the movie, too) turned into a 30-minute conversation about way more substantial things than a pink-filled cinematic masterpiece.
The “same kind of different as me” principle. Peter Thiel talks about this in Zero to One. Especially in the early days, everyone is bound together by being different but in a similar way. An example from one random startup is that many people went to one college south of Silicon Slopes / Lehi, UT and now all root for their alma mater’s nemesis football team north of there. (If you’re local to Utah, you’ll easily fill in the blanks on the teams.)
Let’s groooooow! Most everyone is gleefully throwing themselves into the deep end and doing work they’ve never done before in a context no one has ever conceived. As Thiel writes, “A startup is the largest group of people you can convince of a plan to build a different future.” This requires a growth mindset and, again, humility. A willingness to let go of control, pretense, or ego. Humility and vulnerability are best friends. Embracing both fosters empathy for others and deeper connections.
Side note: I have found the research on best friends at work to be true my whole career. In fact, much of my non-neighbor social circle is a beautifully crafted patchwork of former co-workers.
“Gallup has repeatedly shown that having best friends at work is key to employee engagement and job success. Gallup data indicate that having a best friend at work is strongly linked to business outcomes, including profitability, safety, inventory control and retention. Employees who have a best friend at work are significantly more likely to:
engage customers and internal partners
get more done in less time
support a safe workplace with fewer accidents and reliability concerns
innovate and share ideas
have fun while at work”
Ask yourself: Do you have a best friend (or two or three) at work? If not, I would highly encourage you to take the time to make one or consider that it might be a signal you would be happier somewhere else.
#4 You don’t have patience for people who have never done their current job before.
Part of the startup scrappiness means new opportunities arise all the time that require the currently available employees to jump in and figure them out together. And that includes the CEO/founder or co-founders. They’ve never built this type of company to this stage before in these (whatever they are at the time) macroeconomic conditions, on their own. If it’s their first time, it is 99%+ of people’s first time.
If you are someone with some or decades of previous experience, the best thing you can be is patient. What does this look like in practice?
Give yourself and everyone around you a lot of grace. This doesn’t mean don’t performance manage people up or out. It means it may take longer and the hire slow, fire fast principle doesn’t always apply at a startup.
Be a trusted sounding board, a cheerleader, a guide, a coach, a mentor, a sponsor, even a friend.
Recognize you may have experience but you don’t have all the context. Be curious, ask questions.
Look for the positive in everything being attempted and especially celebrate where there are bright spots and successes.
Sometimes you have to be “the adult in the room.” Stay focused on the big picture and don’t “major in the minors.”
Be the person who implements a solution. It’s not enough to follow the classic “bring the solution, not the problem” adage and definitely don’t be someone who is just pointing out problems. If you want to be a problem-pointer-outer, Series A probably isn’t for you. (Larger companies are filled with people who thrive as “The Impatient Auditor” and they are often revered but suuuuuuuck to work with.)
#5 You get bored or annoyed easily listening to the core group relive the early years.
The core group may be the first 10 employees or the first 50. It’s definitely anyone who is referred to as “the unofficial 3rd [or 4th or 5th] founder.” It’s the group who consistently re-hashes memories and inside jokes you and most of your current co-workers weren’t there for.
Here’s the thing . . .
A startup’s “When we were first starting out . . .” mythos is sacred. Yep, you read me right. Sacred. Yes, Series A executive teams and senior leaders should work hard to create an inclusive culture as the company grows. Part of that, though, is ensuring everyone knows the stories. And by that I mean don’t make a shorthand reference to a “tale from our first year” in a large group, laugh, and quickly move on. Explain what’s funny and why. In detail. Share the stories and then share them again and then share them again. And again. And keep making new memories and share those. And you don’t have to apologize for re-sharing or caveat everything with “Some of you have already heard this . . .”
If you, as a new hire, can’t abide feeling a little on the outside as employee #51 or later, don’t join a Series A.
#6 You think that just because startups “move fast,” all your ideas will be greenlit.
It is true and thrilling that startups move fast. But there’s still going to be friction getting new proposals going. I love eternally-optimistic ideas people. I am also an advocate for diversity of thought, different approaches, risk mitigation strategies, and having a “bad idea” or “devil’s advocate” person in almost every room, especially when you’re making big, make-or-break decisions. It’s also true that it can be downright depressing and deflating when you have even one Eeyore-like person with any amount of influence or in a leadership position who operates from a place of negativity as their default. This is also hard because a person who orients to this mentality more often than not won’t realize that they’re “that person” in the room.
How do you help your ideas take root and counteract any potentially fixed mindsets at a startup?
It’s not easy but here are a few tips I’ve learned. (This list is also applicable at other sized companies.)
Propose (especially radically) new ideas 1:1. This is critical. Don’t spring it on them in a group setting unless you’re prepared for or want the fallout for some strategic purpose.
Ease them in to anything new. Qualify, qualify, qualify. “I’d like to try something new. I’m not sure if it will resonate at this company or with the team, at our stage of growth, but I’d love to walk you through my thinking and get your thoughts.”
Getting real tactical here. . . . Let them know upfront how you’d like them to show up in the conversation. “I want to make a proposal. The most helpful way you can engage with me at this stage is to provide candid feedback and have an open dialogue with me—not make decisions just yet—about both 1) what is realistic and possible if we take an optimistic view and then 2) expressing the top concerns you have and why.” It may feel awkward to say this, especially if you’re talking to a senior or executive leader or the CEO/founder. The best ones will welcome it.
Conversely, let them know that you don’t need their opinion right away. That they can take time to absorb what you’re saying and you can schedule more time to discuss at a later date.
Be the one to bring up issues or possible risks first. Have a plan to mitigate them.
When they inevitably say “that will never work” or some variation of that, acknowledge it by asking questions. Don’t address their concerns head on or dismiss their concerns; this can be construed as defensive (especially if you’re a woman in tech!). It’s fascinating to me that often when I start to ask genuine, thoughtful questions, they soften almost immediately and start to see what’s possible.
Socialize it ahead of time with people they listen to or people whose opinions they highly value. Use this to your advantage. “I briefly ran this by so-and-so and they really loved the idea.” This may feel underhanded or like you are manipulating the person. But it’s really about intent first and foremost and about you doing your due diligence, giving them the freedom to react with all the information—including who is already familiar with your proposal so they feel more confident doing their own probing afterward.
This one is unfortunate that I even have to say it but you also may need to get one of the people they trust implicitly to present or co-sign on the proposal in a formal meeting. Especially if you’re a woman in tech talking to a male leader in tech. The Authority Gap is real, people. It absolutely sucks and makes you want to sit in a corner and cry and tear your hair out some days. Again, it’s about building rapport. Hopefully you won’t have to do this more than a few times before they listen to you directly.
The main research-backed premise of the book is that women do not have the same authority and credibility as men in the workplace until they reach the C-suite. Not Director level, not VP or SVP level. C-suite level. And there aren’t many of those opportunities for underrepresented groups at the present moment. Please read the first chapter before forming an opinion based on the title. It’s dense and a little—really, a lot—maddening to read, so no judgment if it takes you a while to get through it. It’s another one of those “We haven’t made much progress, ladies” reality checks. In the spirit of positivity, the more people of all genders who read it and internalize it, the more likely we are to accelerate change.
Related to qualifying, start small. Frame your idea or proposal as “What if we were to try this piece first and see how it goes (i.e., gather some early evidence)?” The opposite may also be effective—somewhat overwhelming them with your level of preparation and the depth of your proposal—especially after you’ve built rapport or have a few “getting them to yes”-es under your belt. This can work especially well for leaders who are data-driven.
Side note: Sometimes a version of “be positive” makes its way into a company’s core values. I take umbrage with this and companies who have a core value of any “Don’t be a jerk” flavor. These are right-to-play values rooted in Respect and can be highly gendered. If you haven’t read How to Succeed without Hurting Men’s Feelings by Sarah Cooper (and I’m talking to everyone — women, men, non-binary) pick up your copy today. It’s a great way to build empathy and pee your pants from laughing too hard.
Another side note: I love the word ‘umbrage’ but I do try to use it sparingly. “The word has its roots in the Latin ‘umbraticum,’ meaning ‘of shade or shadow.’ [So cool.] Over time, the connection to shade or shadow led to the metaphorical usage relating to feelings of offense or being overshadowed by another's actions or words.” (ChatGPT)
#7 For Product leaders: The extreme sport of altitude-jumping doesn’t thrill you to your core.
What is “altitude-jumping?” The best example for a Product leader is going from answering an Engineer’s question about a specific user story you wrote at 6 am as part of a 5-page PRD and then presenting the 3-year product vision and strategy to the Board of Directors for two hours. This was my week last week.
Here’s some cold, hard truth. Let’s be real for a minute.
We throw around the phrase “player-coach” like it’s so simple to do and always a good thing. It’s not a good thing if you’re a company just trying to save money on actually paying your best people what they are worth as experienced, effective, impactful, indispensable and strategic leaders.
Player-coach roles can be a good, short-term thing if you want to give someone less experienced, or with no prior experience, a chance to prove themselves in people leadership. Very common in a Series A through even Series E. If you have several or all player-coaches in one department, time to look closely at your org design. That’s the definition of inefficiency.
(And, btw, I know this might run antithetical to the whole “jump in and do whatever is needed,” even the menial tasks, at a startup. That’s not what I’m referring to here. No one at a startup should be above any one task or not be able to jump in and help because something is “beneath them.” Of course not. This is about sustainability and what’s appropriate longer-term.)
I sign up for player-coach partly because it’s a way to gain traction, especially as a woman in tech.
Women don’t generally get promoted based on our potential like men do; we get promoted based on what we’ve spent our blood, sweat, and tears proving.
And before anyone scoffs at this or takes “umbrage,” 1) it’s backed by research like this (and then there’s this too); and 2) please take a minute to get curious and build some empathy. Ask any woman you work with. Any woman. She will rattle off at least three examples of this playing out in her own career. (Watching men “fail up” is real, too.) I’ve been doing this for a while and it continues to be true over and over and over again. I haven’t thrown in the towel just yet but some days (sigh) it takes a lot of mental fortitude to keep going.
Being a player-coach requires passion for altitude-jumping, which I do enjoy. For a short time. Not for more than 6-12 months. Because it’s mentally exhausting. And any more than a year, you are being taken advantage of. And I mean that sincerely for women or men. It may not be malicious or intentional but it’s real and shouldn’t be taken lightly. After a year, you either officially promote the player-coach or make them an IC (Individual Contributor) again or exit them.
In my career, I have always—and I mean always—joined companies as an IC or a player-coach with a very small team and within months been asked to start forming a team or otherwise take on more responsibility. Often times a lot more responsibility. And often times without the title or comp change to match. I’m not complaining but shedding light on a pattern that I experience and others may relate to. When did it become the norm to have to do the job you might be promoted into for at least a year or as an “interim” leader before you earn the right to be fairly compensated? I share this umbrage on behalf of all of us. (Okay, maybe I don’t just use it sparingly.)
Back to altitude-jumping. You either love it or hate it. If it’s the latter, don’t join a Series A. If you do join a Series A as an altitude-jumping player-coach, be sure to get alignment before joining on how long you’re expected to wear the parachute and the rocket pack.
#8 Most importantly for Product leaders: You have conviction that you own the final decision on product vision, strategy, roadmap.
Another way to state this is “If you can’t wait until you know better than the founder or co-founders.”
You won’t. Ever.
In the same way that I think the company’s stories are sacred, you must have a fundamental respect for your founders. They’re the ones who took the risk, especially if they bootstrapped it. They’re the ones who saw a future no one else could see. They’re the ones who now have 50-100+ employees relying on them and their decision-making for a paycheck. And, remember, they’ve never done this before.
Sometimes this respect can play out as deference, but not always. As a Product leader, you must form a strong, data-backed POV. You must influence and drip campaign your way to changing minds. But you don’t get to make the final decisions.
Your job is to bring disparate views about the product direction together, simplify them and make them make sense, get everyone aligned, and recommend a compelling product vision, strategy and adaptive roadmap. You are the master broker and the master communicator and the master advocate of all things Product. Do your homework, get inside the minds of your founder(s), don’t waste people’s time, and you’ll earn more and more autonomy and trust.
It makes me a little crazy when I hear HoPs (Heads of Product) complain about how difficult their founder is to work with or how immature they behave. How they are always an obstacle. Wrong mindset. If you don’t respect the founder(s), don’t join their Series A company.
#9 For all leaders: You have a pre-defined “To be successful, I need . . .” list.
You should absolutely fully understand what you’re getting into. But Series A is not the time to be ultra-demanding about specific headcount, reporting structure, budget, title, decision rights before you get your foot in the door. A light touch, equanimity, and navigating and negotiating through influence once you join will always win out. Be water, my friend.
Put another way, “Don’t focus on being successful. Focus on being useful.” —Peter Drucker, The Effective Executive
#10 You read this Top 10 list expecting there would be exactly 10 things on the list.
At a Series A, expect the unexpected! (See #1)
In conclusion
To recap, here are the Top 10 reasons you should NOT join a Series A:
You need certainty and control and struggle with change.
You feel most valued when you are highly specialized in your role, not a generalist.
You hate getting deeply personal with co-workers.
You don’t have patience for people who have never done their current job before.
You get bored or annoyed easily listening to the core group relive the early years.
You think that just because startups “move fast,” all your ideas will be greenlit.
For Product leaders: The extreme sport of altitude-jumping doesn’t thrill you to your core.
Most importantly for Product leaders: You have conviction that you own the final decision on product vision, strategy, roadmap.
For all leaders: You have a pre-defined “To be successful, I need . . .” list.
You read this Top 10 list expecting there would be exactly 10 things on the list. (Expect the unexpected!)
If you still aren’t sure if Series A is right for you, drop me a note on LinkedIn! Happy to connect and chat.
And you may be wondering, with this Top 10 list and all the parenthetical asides (there were soooooo many, huh?), “Wait, are you still glad you joined a Series A?”
Absolutely!! Because . . .
I am a variety- and change-seeking multipotentialite who is known for being “real;” generally patient and interested in all “the early days” stories; eager to find a way to “Yes” or “And” and create with possibility; love altitude-jumping (as long as there is a light at the end of the tunnel); I have great respect for founders’ visions; I focus on being useful, not just successful; and I have come to expect the unexpected.
I love reason #10, but all of these are very accurate! And although startup land feels like it could be a scene from Meg 2 right now, I can't think of a better way to start your tech startup career than navigating the challenges we are currently experiencing. These challenges are going to serve as critical experiences for driving innovation in the future with long-term sustainability!