Strategy and Operations
I’d predict that Beth from The Queen’s Gambit will exit chess to become a Strategy & Ops lead at DocuSign.
I remember in college when ‘strategy’ was the coolest thing for a business student to do. Not sales, marketing, or other functions that make a business run. Strategy superseded those roles; you aren’t just driving the company’s growth, you’re plotting how to drive the company’s growth. When I first started a career in tech back in 2015, strategy felt like it was the end goal.
Earlier this year, when I felt that freelancing as a growth marketer was becoming less challenging, I started to search for new roles. ‘Strategy’ roles were of immediate interest: General Manager of a line of business or Special Projects at a high-growth tech company. It would leverage my growth knowledge, but challenge me to think outside of my comfort zone.
It also, in most roles, encompassed ‘Operations’: now that you have an idea, how do you put it into practice, make it efficient, and ensure it’s scalable? I searched for 3-4 months while running my growth agency, having some of the most absurd interactions with supposedly reputable startups (which I’ll write about soon). I also had some amazing conversations: some early-stage startups where the role was less defined, and some ‘growth stage’ startups where I’d have to prove myself before getting big responsibility. At the end, I was grateful to find a fit with Shiftsmart, a Series A startup that helped companies source, hire, train, and manage shift workers.
In this post, I’ll talk through my experience in a ‘Strategy and Operations’ role, what I learned, and why, in the end, it wasn’t a long-term fit. Quick recap below:
Operations is a skill set that allows you to efficiency scale an existing system — I thought it was necessary for me to learn so I could scale my agency + build other ventures
Company, manager, product, and role are all considerations in what makes a great fit, and why I signed on with Shiftsmart
I needed to get my hands dirty to succeed at an early-stage org — it’s often 30% Strategy and 70% Operations
If I’m not naturally motivated / excited by the problems I’m tackling, I won’t succeed in tackling them
If I can’t connect the skills I’m learning to immediate uses / goals, it’s hard to justify learning them (even if they’re worth learning in general)
Opportunity cost varies for everyone: a good decision for me could be horrible for you, and vice-versa
Why Strategy & Ops?
I’d like to consider myself a fairly well-rounded founder. I’ve held a variety of growth marketing roles (my specialty), but I’ve also done sales, revenue operations, and (as with any early-stage company) a mix of everything else. I recognize I have my blind spots: I don’t know how to code, and while I understand design/product I don’t have any formal background in it.
Most founders who aren’t on Indie Hacker realize they need to make trade-offs; you’ll never be great at everything, so what do you need to know to succeed as a founder? For me, that felt like operations. I could stand up a business and make it profitable, but how do I scale it to 5, 10, 50, 500 employees? How do I remove myself from the day-to-day and effectively manage other functions?
This is why I drifted towards Strategy & Operations. I wanted to understand how an operationally heavy company worked, how to improve my operations skill set, and how to incorporate those learnings into current & future business ventures.
Shiftsmart felt like a perfect fit: in terms of company, my direct manager, product, and role. Let’s break down what exactly that means:
Company
Shiftsmart was well-established ($22.5M in funding, ~ 60 employees), which meant there was structure and I didn’t have to compromise on compensation. They were also early enough that there was lots of white space to tackle: if I could make a case for tackling a problem, it was likely I would get the responsibility + resources to do it.
Manager
In any role, your direct manager is a huge part of whether the role is a good fit or not. I had known my boss, Rob, for a few years as a good friend + mentor, and his background was incredible (built operations at Airbnb & Siteminder, a unicorn Australia tech company). I respected him a lot and felt like I could learn a lot from him, which made this a great fit.
Product
Shiftsmart is tackling a very interesting space: labor. Like Uber, Instacart, or other labor-driven companies, this comes with its own set of unique challenges. I knew first-hand as a freelancer and agency owner that fractional / part-time labor had grown significantly in the last 5 years. This was even more pronounced for blue collar workers: work 20 hours at Target, 20 hours at Amazon’s warehouse, and another 10 as a delivery guy. Shiftsmart was creating the first marketplace where you knew whether a worker was reliable, what they could do, and gave you the tools (both ops + product) to easily hire & manage them.
Role
My boss was very generous with my offer — I had actually applied for a Biz Ops / Analytics role on the team but wasn’t a fit, and he offered a 3-month, full-time contract where I could join the team (growth / ops) and see where I fit in best. This was perfect for me: I could transition my agency to part-time, feel out the org / culture, and hopefully convert to permanent full-time if everything worked out. More importantly, the role itself was operations-driven (‘how do we screen / evaluate our workers’), something that I had never done before.
Strategy (and Operations)
In the first 6 weeks, I fleshed out a few growth projects for the team (referral program, retargeting) and built the screening process for a new client. Given how fast Shiftsmart was growing (my team didn’t exist in March), my role quickly evolved to be solely screening (recruitment) driven. How do we build a process to intake and evaluate workers at scale, across multiple roles?
I told my boss when I joined that an area of improvement was closing out projects — I could stand up and take a project 80% of the way, but transitioning it to other team members and building processes so it could be efficient was a challenge. This was a similar case with screening: ‘strategy’ was less of challenge. I made a matrix to evaluate workers, built scoring criteria, and found ways that we could screen workers at scale.
‘Operations’ was a different story. During our weekly stand-ups, my boss/team often had questions that I didn’t know the answers to. I’d start a project without a clear set of metrics to track, and as a result, avoided a system where I could easily see what went wrong + how to track it. So when I built a call center that had a full team of agents and made thousands of calls per day, identifying the biggest areas to improve was a taxing challenge.
Prior to this role, I had always glorified Strategy & Operations. And perhaps I was right — I’m sure the same role at Google, Shopify (where I used to work), or other big companies would be drastically different, where thinking through problems and creating plans would be the big obstacle to overcome. But at Shiftsmart (and I’d assume at other early-stage orgs), ‘Strategy & Operations’ was 30% strategy and 70% operations. I never worked a shift on the platform. I didn’t call 20 applicants myself to see how the script would work. Getting my hands ‘dirty’ was essential to succeeding in such a role, something I didn’t realize until later.
What makes a good fit?
My contract was extended a month (4 months in total) to tackle screening and see if I could run the function long-term for Shiftsmart. The last 3 weeks were especially gruelling, due to problems that I’d imagine a lot of people face in high-impact roles at high-growth companies: imposter syndrome, not focusing on the right problems, and leaning on my team/resources less than I should have.
The conclusion I came to, after a long chat with my boss and several good friends, was both illuminating and confusing. I confirmed that I knew what needed to be done to succeed in my role. I also confirmed that while there was a skills gap, it was NOT one that was insurmountable. But I wasn’t happy with my role / the work that I was doing, and I felt like I was burning out. So where does that leave me?
My friend Thenuka gave me some great advice that I’ll paraphrase poorly below:
“You need to be excited about the problems you’re tackling. Calling them interesting or worth solving isn’t enough. If that’s not the case, you’ll have a hard time.”
The team, product, boss, and organization can be amazing. In a lot of ways, Shiftsmart was. But I didn’t get energy / get excited from the problems that I needed to tackle. I could acknowledge they were interesting and worth solving — I could even see how solving them would make the job an even more rewarding one. But if it wasn’t a problem that I was naturally motivated to solve, any obstacle would be 10x harder to overcome.
The second area to focus on is “What is worth learning… Now?”. Remember in school when you’d take a mandatory class/credit and not realize why it was necessary? I always found those courses especially challenging. If there wasn’t a practice / visible (near-term) use for the knowledge, it was harder to justify learning it.
I believe that work is no different. It amazed me how efficient Shiftsmart was as an organization. Each department functioned like its own company. Unlike my prior experience in B2B SaaS, almost everyone came from consulting, banking, or an operationally-heavy company (Uber, Lyft, etc.). I can say with the utmost certainty that ‘operations management’ (to simplify it) is a skill that is VERY useful and one that I’ll need in the future.
But do I need it now? In the next 3 years? It was harder to make this argument with myself, which made it harder to justify the role. I needed to know why learning a useful skill was good FOR ME, not good in general. I have no doubt that I’ll revisit it in the future, but only once it’s necessary for me to grow + accomplish the goals I set out.
Opportunity Cost
A final point here is around opportunity cost. For every decision I make, there are other decisions I could have made. Returning to school and leaving a high-growth company with amazing culture was a decision I made. Choosing to start an agency instead of joining a startup was a decision I made. Picking Toronto as my home base, and not New York City, Los Angeles, or San Francisco was a decision I made. They all come with an opportunity cost, and I’m aware of that.
Maybe in a different life if I was entering tech and dead set on strategy/ops (i.e. ‘exiting’ from another firm), I would have stuck around and persevered. But opportunity cost is real: since August, my full-time job (Divisional) became a side hustle which made me more than the new full-time job I had chosen. The team grew from 3 to 10, we hired an amazing full-time PM, and our client base expanded. In Q1, we’ll be making 3 more full-time hires and scaling to 15 employees with 100% revenue growth from Q4 2020.
I’m a growth marketer and a founder. I know what I’m good at, what I need to get better at, and how that all plays into my 3-5-10-20 year goals. Just as some people leave their full-time jobs to pursue a side hustle that’s growing rapidly, I chose to revisit my side hustle, invest more into ongoing projects, and continue to build. That’s an opportunity cost that wasn’t easy to swallow, but a decision that I’m comfortable taking.
Conclusion
‘Strategy & Operations’ will forever be a sexy position. It’s cool to quarterback the growth of a company, especially if your past role / skill set makes that a natural transition. Unfortunately, it wasn’t the greatest long-term fit for me. But I’m forever thankful to Rob & the Shiftsmart team for giving me the opportunity, and I’m proud of what I built while I was there. And if you’re looking for a great place to work and love operational challenges, Shiftsmart is hiring rapidly. If you’re a growth marketer and looking to tackle new problems, drop me a note because we’re hiring rapidly as well!