Here’s some advice on picking your trajectory in the high-tech startup scene if you didn’t go to MIT, Harvard, or Stanford. (Read: Startup vs MBA) This article is mainly for folks who want to get out of one career path and into the tech startup scene and are ambitious, aggressive, or competitive enough to want to quickly be in a leadership role. My advice: start someplace big then go small.
I started off in the United States Navy. It doesn’t get much bigger or more bureaucratic than that. Big companies or government organizations can afford to train you – something almost unheard of at early stage startups. You aren’t thrown to the wolves in a massive org – you are part of a well-defined pipeline to make you into a valuable contributor. Plus, they have tons of programs to allow you to self-educate further. Most people never take advantage of these opportunities because it isn’t directly rewarded by huge companies. Use this time to build skill sets and grow when the consequences of something going wrong are pretty low.
Your natural instinct after spending a couple years in ultra-enterprise companies or the government will probably be to go to a Mid-Market or a just IPOed corporation. If a company has 500+ employees, they’ll probably pay market or better in terms of compensation packages. While this may lead to the most stable, high and predictable income stream, it is unlikely to get you to tunnel into some next-level opportunities. The smartest play would probably be to find a Product Management job and work your way up in one of these mid-market companies. I’m going to recommend another path.
In my mind, the best way to get noticed and move up quickly is to be at the pointy end of the spear (to revert back to my Navy days’ terminology). In business, the pointy end of the spear is Product Management and Sales. Defining what gets built and figuring out how to monetize it is the game in Silicon Valley. Am I saying engineering, marketing, finance, people operations, or any of the other necessary parts of the organization aren’t as important? ABSOLUTELY NOT! In building a company, 10X talent in each of those organizations is paramount. In my opinion, being a great individual contributor in engineering, data science, or artificial intelligence is the most empowering place to be, but it isn’t the quickest setup to get into a company’s leadership team.
A solid career choice then is to be as close to the customer as possible and define as much of the product to drive sales as possible. The obvious career path is product management, but this article wouldn’t be “sneaking in” with obvious advice.
If you go to a smaller company, that has just proven broad-based product market fit, as a Solutions Architect (SA), Sales Engineer (SE), or Solutions Consultant (SC), then you get a pretty cool opportunity. You get tons of interactions with customers – more than almost any other group, except maybe SDRs, AEs, CSMs, and support. You may not get the same “pure” customer interactions that Product Managers and UX/CX people strive to get in not biasing customers, but great solutions sellers can normally tell when they are doing a good job selling in spite of product functionality holes.
Plus, at a smaller company SCs, SAs, or SEs are normally player-coach type roles. You influence how AEs run sales cycles, you must have deep relationships with product to sell in-line with the roadmap, and you’ll normally have pretty good back channels with engineering to figure out how stuff really works where the rubber meets the road. These teams scale pretty rapidly and drive revenue influence. This is one of the few positions where you can jump-in and move pretty quickly. Sales as a whole is a grind where you have to prove yourself quarter over quarter. Product management can only release so many products or features at any given time. Solutions salesman can get 4-5 at bats with customers per day defining and then refining pitches and figuring out what matters to who. It’s all about taking a static product and communicating that feature set in a way to more broadly achieve product-market-fit than would otherwise be possible.
If you have a feel for what the customer wants and know how to communicate that to prospects and customers, this is the tunnel to the leadership team. (Read: Why I Started Truthlab) Once you know that what you are building is what customers want, you know roughly what the ASP will be, and how big that market is and then much of the work is down to execution. If a diverse, strong leadership team is in place and some decent capital has been raised, then knowing what to build and how to sell it is the golden ticket.
In summation, the quickest way to sneak into leadership at a SaaS company is to best understand the customer. And one of the quickest paths to understanding the customer-to-product market-fit mapping is being a Solutions Consultant, Sales Engineer, or Solutions Architect.