From Sales Rep to CRO in 10 years
The often unspoken highs, lows and sacrifices
I went from being a sales rep in the UK to CRO in Silicon Valley in approximately 10 years.
In that time I grew sales by ~$20m across to 2 early-stage startups, grew a 3rd even faster and last year started my own company for the first time.
But what you don’t see on Linkedin of my backstory, or that of many others that have managed to scale some heights in startup land, is the struggle they went through to get there.
Here’s a synopsis of the 10-year journey that led me to California’s Bay Area.
My Potted Journey
1) After a life-threatening illness I returned to a startup a month ahead of doctor’s orders in order to keep building, only to discover after 4 years of commitment and strong results, the startup had decided to re-org and my role was “no longer needed”, and furthermore most of my vested share options were “clawed back”.
2) I made close to nothing from a $180m exit that happened 2 years later, despite leading that startup from ~$0 to $20m in ARR.
3) After that experience I had to work hard to maintain my faith in human nature and vowed to never give up on myself or my dreams, despite this setback.
4) I chose to join a Silicon Valley HQ’d startup as their first hire in EMEA on $0 salary for the first 3 months, then 75% under market for next year, because together we decided to bootstrap vs take VC funding - in return I took a higher equity stake than normal, and because of this I saw myself as much as an investor as an employee.
5) The CEO promised me that if this gamble went well, he'd help me fulfil my dream of moving to California and helping him lead the company's growth
- it would have been MUCH easier for me to be sceptical of this promise given my recent past experience, but that's not how I roll, and anyway, there was something different about this founder.
6) To afford to work at that startup, I slept on the lounge floor of my 1 bedroom 500 sq ft apartment in London for 2 years so my wife and our newborn daughter had the night's sleep they and we all needed.
7) I built this startup from the ground up in Europe, I did everything, including building the office furniture and taking out the trash. And I loved every minute of it. EMEA outpaced the growth of the US within 2.5 years.
Fig 1: The Guidebook EMEA Office on Marshall Street - before I built the desks!
8) After 2 years, we were building momentum and I could justify getting paid close to the market rate and was able to upgrade to a 2-bed apartment and sleep in a real bed again.
Fig 2: Building awareness: The first podcast for Guidebook in Europe
9) In 2017, I moved me and my wife, daughter and our 3-month old son to California to lead the global growth of said startup as CRO - the CEO came good on his promise 👊🏼
10) In 2020, I left Guidebook on great terms with the founders and investors and went on to have an incredibly successful 12-month stint as CRO at an a16z-backed startup.
The lessons:
In 2021 I started a consulting practice to teach founders at scale, how to successfully evolve from founder-led sales, something I'd now done successfully 3x back-to-back.
There are many highs and many lows on the journey that got me here and there were many great people I met along the way and let’s be honest some real assholes too.
Here are a few lessons I’ve learned:
1) Have faith in yourself, back yourself, and filter out the naysayers
- the naysayers might be your closest friends (or maybe even family members!), stay determined, focus on your dreams, commit and you’ve got a shot.
- You’ll always face setbacks, and if you are not screwed over at some point on the journey you got lucky, it’s saddening to discover just how common those that have committed and performed get treated poorly. It seems to happen a lot in sales, especially in early-stage startups. I have thoughts on the reasons why, but that’s for a different post!
2) Play the long game, it's a process
- Take a 5-year view, maybe longer if you can. If you believe in yourself, you'll appreciate there's a process to success, and as time passes momentum eventually builds, and it does get easier, even if it’s never easy.
- This doesn’t mean doing a job for 5 years, this means setting yourself an ambitious goal for 5 years in the future, super ambitious, and see if you can get there.
3) Surround yourself with good people, that have your back
- Some people are clearly out for themselves and will stop at nothing to further their own personal cause, their bank account or their ego. These are not people I identify with, however, I have had the misfortune of trusting in people who turned out to be these types.
- Other people take pride in seeing others succeed with them. They understand success is both more likely and more rewarding when they invest in others to help them on their journey. This is not to say these people are not ultra-ambitious, want to make a shit-ton of cash or make an indelible positive mark on the world, it’s just that they go about it differently from the first bunch. This is the type of founder and leader I identify with and spend my time with these days.
4) You are not your company
- Startups have this knack of being all-consuming, and I fell into that all-in trap in one where I led sales. Don’t do that, it’s not your company, never forget that. Be committed, but identify as something other than your startup. Founders should also take this advice, in order to better manage their mental health.
- For me, I identify as a father, husband, son, and brother and I identify as a runner and generally as an athlete - although there’s some work to do on the physical fitness side of things! This means I care about my diet, my well-being and both my physical and mental health. This all comes ahead of my work, including ahead of my consulting practice, or at least that’s my daily intention!
Whatever you identify as be deliberate about it, give time in the day and week to dedicate to it, and don’t let your work get in the way of that - whether you’re a founder or a sales rep. Some of you are better than others at this, I was terrible at it, the worst, but I’m much better now.
5) Start a side-hustle today
Getting my consulting practice off the ground has been fun, but not easy, especially for someone like me who prides himself on high-quality work.
If I had my time again, I would do the following:
a) much more actively build my Linkedin following
b) proactively engage with people on Linkedin
c) write at least once a month on my own personal blog
d) attend more meetups and engage in more communities
e) do some free consultancy work
f) evolve that consulting from free to paid, it happens naturally if you do good work.
I essentially did NONE of this prior to starting my practice, so whilst I have the experience, I didn’t have the network. It felt like the extreme version of Reid Hoffman’s “building the plane as you’re flying it”.
Whether I build this consulting practice into perpetuity or go back into startup land as an operator remains to be seen, but one thing is for sure - I’ll always be side hustling from this point onwards.
To wrap up
Journeys come in all shapes and sizes. Suffering and sacrifice are part of any journey worthwhile taking, but so are balance and joy.
When you see a seasoned C-suite executive, who has the scars of sustained results under their belt, there’s nothing more valuable than learning about their journey.
Most of my work today is about encapsulating my stories in business and telling them in a way that captures both the imagination and curiosity of my clients.
From there we riff on how to use my experiences as proxies for their own business, but ultimately, the value I deliver is in my experiences re-told, and re-worked.
If you do one thing for me this week, please seek out a C-suite exec and ask them about their journey - some of those stories might prove the spark you are looking for.
Take care folks!
Wayne
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Twitter: @waynegmorris
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