Pt 1: How did I get into RevOps
Today's article is going to be a different. Instead of a pragmatic RevOps newsletter I'm going to instead reflect on a 20 year career. What I've learned. It's more for me to jot down my own thoughts. Maybe you'll learn something from it. Maybe you won't. Sorry if you don’t. Either way if you’re open to it I’d love to hear your story also (reply to the newsletter!)
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What I learned from poker
In poker you might have the best hand but then lose because of the luck of the draw. I play a variant of poker called Texas Hold’em.
Let me explain.
Every player receives two cards.
On the table are three cards (called “the flop”) turned downwards. The dealer turns those cards over once all bets are placed.
You may decide to up the ante and place a bet or you may decide to stand pat if no one has placed a bet. If someone has bet and you don't like your chances then you can fold your hand.
The fourth card hits the table is called “the turn”. The same game theory of decisions plays out on whether to bet, call (stay), or fold.
The fifth card is called “the river”. Same back and forth of information reaches you and time for you to make a few decisions.
By now you've collected all sorts of information. You assess what your move is going to be at every moment of the game. You don't know how things will turn out. Only that you will be able to look back in hindsight once the hand is over to see if you've made the right decisions or not.
I feel that life is like this. Careers are like this.
It's all one big poker simulation.
What do careers have to do with poker?
When we're children we're asked “what do you want to be when you grow up?” Kids will say something topical like…
Fireman! Or firewoman???
Police officer!
Doctor!
No one and I mean no one ever says REVENUE OPERATIONS VP!
Tell me I'm wrong. I'll fight you on this.
If your child says this at school unsolicited let me know so I can feature them on my newsletter.
Okay so where am I going with poker and careers. When we decide (or stumble into) getting into Revenue Operations there’s unlikely to be an intentional game plan. We like doing this type of work. Simple as that.
Or maybe you like my newsletter so much you’ve decided to gamble your life on my advice. Good for you.
There’s curiosity in problem solving like a moth to a flame
There’s joy in seeing a problem through to a solution
There’s grit in doggedly applying oneself to an intractable problem
When we move up via promotion or decide to move to a new company there’s a lot of unknowns.
Am I fairly being treated? Compensated? Supported?
Is this a dead end path or a stepping stone to truly something bigger?
Is this company a winner?
We think we know (each round of poker) but ultimately we don’t really know (the river). When it’s all said and done and you hit that big red “retirement” button you can look back at your career to see how it all played out. Almost like being Charles Dickens’ Ebenezer Scrooge visiting his past self.
The accounting of life will be done.
We go to university. We get a job. We get promoted. We change jobs. Etc. Each sentence is a round of poker. In between each round is the information we have to work with. Make bets. Find out if it’ll work out.
Reducing information asymmetry as much as possible
The odds are against you at every turn. You just don’t have perfect information. We have to make judgment calls all along the way. It’s best to de-risk the information gaps as much as possible. That’s why it’s important to have questions ready at the end of each interview. And to answer the questions about yourself.
What is the narrative and vision I have of myself?
What goals do I have set?
How ambitious should I be? Should I focus on having a more balanced life?
How does this or do these opportunities before me help me close the gap to my goals?
If you can answer all of these with clarity then my hat is off to you.
I changed careers a bunch in my 20s because I didn’t know what I wanted
Out of university I went into management consulting with Accenture. I learned a lot.
Project management
Working with difficult and indecisive customers
Dealing with ambiguous requests
Selling oneself as an expert to a customer who thinks you are one
Digging deep into the world of research to find out the answer
Getting really good at excel
Then I went into commercial real estate as a seller. All commission. No salary.
I set up my own CRM using SugarCRM (the firm previously used a rolodex)
I cold called up and down the list of the wealthiest real estate owners in Southern California
I tried to sound professional and experienced (but inside I was quaking and felt like I had no idea what I was talking about)
I ended up with $50M in commercial property listings. The most promising offer I received was for a $12M strip mall with an anchor tenant unit on the corner. At a 2% fee I would have received 50% of 50% of that. That was a $60K commission. This was after a year of hustling.
And it fell through.
And my savings were exhausted.
I had to throw in the towel.
Time to move on
I moved back into management consulting for a Microsoft certified partner. We did mostly Systems Integration type work. It was fun. But then I heard one of my teammates move over to another business unit within the company: the external recruiting agency.
This company had a clever business model. They would set up the systems architecture and implement everything. Then the company would ask if we could stay on or try to poach the consultants. Instead of doing that, the company decided to build out a recruiting agency in house.
Fees were 20% of the first year salary if the hire stayed for 90 days. So if we placed a candidate for $100,000 per year, the company would earn $20K and the recruiter would earn 50% of 50% of that. That’s a $5K commission check.
I asked if I could do a rotation into this group. I was back in sales.
I got into the office at 7 AM every day
I made nearly 100 calls every day
I built relationships with every senior IT leader that was in my name in the CRM
I finished my first year in the top 5 of commission earners. It was fun and exhilarating.
The second year I finished in the top 3. But this time I felt like I hadn’t professionally grown compared to my first year. I was just a lot more efficient.
Turning down a promotion
I was promoted to managing accounts and candidates. Ultimately I turned it down to go to business school. I fancied myself going back into a field that was more numbers or technically oriented. The work I was doing was meaningful to the companies I helped hire candidates and for the candidates I was able to find new jobs. I was also paid well for what I did. Having a salary (compared to real estate!) and commission checks (the feeling of closing a deal is unbelievable) was nice and all, but I wanted something else.
Finance comes calling
In business school I leaned into the finance and strategy tracks. I’ve always been good with numbers. But it was my business strategy classes that I enjoyed the most. Now, only if I could combine these interests together.
Side note: if you’re applying to your MBA let me know. Maybe I can help coach you in. If you’re considering the University of Michigan, Ross School of Business (hello Wolverines!) then let me tell you that you are making an amazing decision.
I won’t go into my stints in finance at depth but I had the opportunity to work with Experian (international expansion strategy), Intel (internal venture capital team), and Google (FP&A, annual planning, supporting marketing/sales as the finance partner).
It’s at Google where I realized I still very much enjoyed sales and marketing even though I was in a finance capacity. Much of the work I did looked and felt like what you would call Sales Operations.
Quota modeling
Territory analysis
Forecasting
Pricing analysis
Total Addressable Market analysis
My time at Google was incredible. We turned a 9 figure business into a 10 figure business. I won an award for improving commission error yields to align with the rates that were in the ads business units. We operated on infrastructure that I would consider laughable for a business of that size. From the outside you probably would look at Google and think “wow! what a well oiled business”. Then you talk to people like me who worked there and you hear about how the business was mashed together with duct tape and bubble gum.
Every business is the same! They all have their problems. It’s what gives me confidence that revenue operations is a career that will take a very, very long time to automate away.
My takeaways before going into Revenue Operations
I LOVE revenue operations as a career. Personally I have plans to become a Chief Operating Officer one day (never stop growing) but for now I absolutely love Go To Market strategy and execution. Building companies is hard but oh so enjoyable.
For ten years I bumbled and stumbled around different jobs in management consulting, real estate, recruiting, and finance. I was all promise but no results. It sucked and I felt failure draped on me like an ugly poncho.
But I did learn a hodgepodge of valuable skills that would eventually pay off in RevOps:
Project management (waterfall and agile)
Excel
Commissions
TAM analysis
Python (automate my workload at Google)
SQL (Google had a data self serve culture)
Prospecting, cold calling, calling
Dealing with shitty CRMs or non-existent CRMs
Big picture thinking
This is literally the definition of a generalist. Getting the opportunity to apply it all in sales operations in the next phase of my career is where I started to feel whole. Brighter days ahead.
I’ll get into it next week with you all. For Paid Members I leave a Sales Ops Leveling template for you behind the paywall.
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