Entrepreneurs, by definition, should be enterprising. The same is true of startups. I mean, the whole reason they both operate outside the traditional salaried existence is because they want to try to do something new, something different and something that can’t be done within the established system.
So, let’s say you work for someone with a startup and the company is growing well. It has been for a while and you feel like your skills could be better used in a new capacity since things have changed and you’re no longer struggling to keep the lights on. Your bosses are busy keeping the momentum going and you recognize an opportunity to stretch your legs and flex your muscles in a new position.
So what do you do? You don’t want to seem ungrateful to the people who have hired you on, and you also don’t want to completely shirk your current duties.
There are a couple schools of thought on how to approach this.
“Companies are a lot like revenue junkies,” says career counselor Roy Cohen. “[They’re] desperate for new ideas that will feed the enormous appetite that drives and sustains business in an intensely competitive market.”
So, if you’ve identified a problem, what helps to start with is to write a proposal. Not too long, not too short. Don’t point out what the company’s current “weaknesses” are; instead you’ll want to identify “opportunities.” And if you want to truly create a new position, Cohen suggests that in the proposal you “do not discuss jobs, openings, or anything even remotely connected [with] a pre-existing role.” The main thing is you want to identify the problems/needs and offer a solution. Cohen suggests not giving the entire solution (“that would be suicide,” he warns).
I’m not so sure about that. I think if you have a pre-existing relationship with a place and already work there, you should be fine laying out what the solutions are because you’re basically writing your own job description.
From there, I’d recommend setting up a meeting — don’t say what it’s about per se up front. Just tell them you want to pitch a big deal, and when you do meet face-to-face (and you really should meet for this sort of thing) you should slide your proposal across the table and talk them through it. Focus on how this can help the company make much more money and why you’re the perfect one to tackle the duties.
From there, it should be clear whether they’re interested or not. If they say no, let it die. If they’re interested, well — we’ll explore that in subsequent posts, you captain of industry.
David Wolinsky is a freelance writer and a lifelong Chicagoan. In addition to currently serving as an interviewer-writer for Adult Swim, he's also a comedy-writing instructor for Second City. He was the Chicago city editor for The Onion A.V. Club where he provided in-depth daily coverage of this city's bustling arts/entertainment scene for half a decade. His first career aspirations were to be a game-show host.