Exited Founder, Now Struggling to Figure out What’s Next!

I have over a decade of experience

my expertise lies in product management, strategy, partnerships, operations, fundraising, value creation, financial planning, go-to-market strategies, and scaling ventures

You're probably not an expert at many or even any of these if you only averaged one year of experience in each area. If you're looking for a FT role, I would try to narrow down your resume. Pick a lane you enjoy or are more skilled at, get some Google certs, and refocus your resume.

Alternately, it's okay to be a generalist, but it's hard to walk into a leadership role at a larger company, where these skills would apply, without a resume of success. You may want to look at getting your MBA and/or more consulting roles.
@theeducator I think I understand your challenge.
First, apply same principles as in your company: cold mailing jobs generally don't work.

Second, figure out your expertize for others: if you were ceo of even a small 10 people company, you know business development in a hacking environment. Then go to small startups and become their cmo or chirf buse dev.

Finally: VCs have generslly no idea whatsoever what it is to build a company. You would be a powerful asset. As principal or analyst or even consult. I promise you, if you know how to tell them they need you, they will jump on it.
Feeling lost, lonely and highly depressed and feeling like I lack a sense of purpose.

Burnout is real, relax and you might want to talk to a therapist.

I had initial success creating a strategy role for myself at a large multibillion dollar bank last year but that was short-lived given the bank lied about a lot of things and therefore I left that role.

How did you land that role? Are you trying the same way with other companies?

Salaried employees often don't leave a job before rhe next one is landed, unless the place is a risk for physical or mental health, or have compliance/legal issues. A company that lied about conditions is not unheard of, that's on it's own doesn't always make leaving immediately a good idea.

optimizing for making money to recoup my bank balance, want to be somewhere or doing something that has an impact, want to work with A-star players and finally feel like I’m learning a ton.

Most of the places I have worked in were a decent compromise on these scales. For example one place had ok money, medium impact and A-C players, but excellent work-life balance. Another place had good money, many A-star players, but little impact and regular chaos.

If your main goal is bank balance, then compromising can shorten the search period.

Maybe one of your challenges is that you are like a jolly joker - can fit into so many places that hiring managers fail to see if you are useful for them.

You might want to pick a few target roles/domains and tailor your CV and your storytelling about yourself to highlight that domain and reduce talking about other expertise or drop those.

If you see some domain specific skill-gaps, then you could work on those.

Since it is difficult to fit you into the regular boxes, I would keep applying to multiple level roles: lead, senior, mid-level and junior.
@thepapist Great feedback definitely have refined my search into a few areas and have tailored resumes and approach for each.

I guess I just need to try a bit different of an approach. I didn’t do what I did with the first role that was through a few mutual connections.

I do admit I left a bit premature. Another lesson learnt
@theeducator You're not the only one, I know several others who've been in a similar spot. Some of them went on to create "startup studios" where they raised some angel money ($1-2M) to continue building startups in an advisory role rather than being a CEO. You'd still be actively involved having to get your hands dirty but at a lower capacity and can spread your bets across a few different ideas and hire people to lead the startups.

If you want to join another company I would think twice about the role. For example: a chief of staff is just a glorified admin where you would be taking on a lot of shit and having to kiss ass to management (often less experienced or impressive as you'd think). Personally as a founder myself, I would find it VERY hard to take on that type of role if you've led companies before. This also applies to some of the other roles you listed (vc associate, strategy, etc)... once you've been your own boss its tough transitioning to a subordinate. Don't underestimate this because you might eventually get more depressed

As for Canada, I couldn't agree more... the tech ecosystem is ass in comparison to the US or Europe. If you can't make the US work, consider other tech cities like London, Berlin, Paris... Not only from a career perspective but also the life experience you'd gain living abroad, even if it's only for a few years (speaking from first hand experience). Lots of interesting EU startups struggling to expand into the US which I'm sure could would value experience like yours.

Keep your head high and if you want any specific advice about building a startup studio or in general moving abroad feel free to DM.
@yuca That’s not what the chief of staff role is. If you think chief of staff is glorified admin you are incorrect. Those jobs are for a PA or EA.

A chief of staff is a highly skilled intelligent generalist who does strategic top board level stuff that the CEO, COO etc don’t have the capacity to do all of themselves. It is a highly regarded role and actually very well suited to someone like OP.
@livelovelaugh 100% agree. Maybe I phrased it poorly. Its far more intellectual than an admin or EA. I guess I was coming from the perspective that you're still essentially the CEO's b*tch. The title sounds great but the work isn't. Sure you're dealing with more interesting topics but at the end of the day you're handed mundane work that management wants to offload. You don't have much say, you just follow orders while working aroudn the clock. Yes it's great for people looking to get experience to eventually start their own companies, but OP's already reached that point. Unless you're a CoS for a really impressive profile I think it's a bad fit for any experienced ex-founder.
@yuca There is a difference though even across titles right? Like a CEO of a 10 person company vs 1000. I’d argue COS at a 1000 person company may even be a harder role where you’d even more. Unfortunately being CEO of your own startup doesn’t automatically put you at that level. Even though it clearly is impressive!
@livelovelaugh Yep there's certainly a difference when you're a CoS of a 1000 company but it's not as fulfilling as you imply. I would still argue being a CEO of a 10 person company is a lot more difficult and rewarding - having seen both sides of it personally. There are some exceptions of course when it comes to iconic CEOs - talking about the Musks, Zuckerbergs of the world (lol). But those opportunities are very rare.
@theeducator Maybe you can try to omit the title CEO for a while. Create resumes that outlines your hands-on skills in specific software and functions, metrics of project//sales achievements and major workplace challenges you resolved. It can be pretty daunting for TA folks sussing out more linear and domain specific talent to filter you in.

As a former headhunter (not in US/Canada), I used to do the opposite, recruit domain experts who wanted in on startups. Seems your struggles are similar. It is a hustle unfortunately.

If I read correctly you've already tweaked a few versions of your resume to fit different roles. And you seem to have a very high profile powerful network that you can definitely tap into.

While it may be a tad uncouth to ask high lvl ppl for leads to a 'job' as a former CEO, honestly it depends how you really feel about it deep down.

eg. as far as titles are regarded these days, it's not so much what it is rather the reputation you've built up over your 2 exits. I recall folks coming out of grad school or in their first job managing no one holding VP/Manager titles, thus a bunch of seasoned hiring managers didn't actually want these faux types, they wanted the real hands on and ppl managers, so I'd skip titles entirely. Which leads to...

Give your prime network a ping. They CAN vouch for your rep. Word of mouth and direct references simply cannot beat an ATS. These are connections you've kept for a purpose :) Ask a select few if they might know a good chief of staff in a bigger org or strategic, operative heads that could give you advice over coffee, use that as a catalsyt to present yourself further. Some of the best roles are created for the right person.

Ps: Burnout is real and you should take care of your emotional wellbeing too. Maybe give it time, or try advising startups like some of the comments put here, you might sense the passion of entrepreneurship come back to you eventually or by then, you'd be a rightful employee with an edge of advising startups! Eitherway it's win win for you.

Best of luck OP!
@theeducator I think the problem is you're missing the thrill of making something from the ground and solving problems that comes with it. I get it because I also feel like this when I dont get to solve complex problems. But as much it is fun , sometimes you really need stop and rest for a while enjoying ordinary things like having a cup of coffee with someone you like and chat about the things you like. I will suggest try to get connect with your old friends and enjoy life for a bit, then you can go again build a startups.

But you'e very intresting, lets chat sometimes
@theeducator I think your main problem is you are unemployable. At many companies, especially larger than scale ups, managers hire to leverage themselves not the company. Everyone has a personal agenda and related goals; and you either seem threatening (being much better than them therefore risking their job security) or not going to stay for long (meaning they need to hire someone when you leave, which you will most likely do without a notice).

Additionally, you don't have a university/college diploma. Many companies have HR policies, where some roles require a bachelor degree. Although a hiring manager might want to hire you, Karen in HR can block the decision by saying hiring a non-university college will diminish company's reputation.

The sad truth is, you won't get a job by applying - so if I were you I would start tapping my network, schedule lunch/coffee meets with everyone.

If the money is scarce, go consulting route, especially early stage startups with young founders. And try to connect founders with investors, and definitely go hard on finder's fee. With 0.5% finder's fee, you will get $5k for every $1M you facilitate. Trust me after 3rd one you will start getting inbounds from a lot of VCs and accelerators.

Also, sadly there are a lot of gaps in your story. Literally it is shocking that you guys (co-founders) were not offered a position at the acquirer after the second exit. Why did they only acquire the company but not the talent? Did they keep any of the employees but pushed only you out? If you were the CEO, you should have managed the communications with the acquirer, why don't you reach out to them for a job? You already sold what you built to them, you should be able to sell yourself as a valuable asset for a time period too.

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