Should You Make the Leap and Sell for a Startup

Ryan Walsh, CEO and Founder
Ryan Walsh, CEO and FounderMay 3, 2021

Considering going to a start-up role? We’re not talking about the 300 person series B ‘startup’, we’re talking about there may only be one or two other sales team members, figure-it-out-as-you-go startup.

For some people, the upside is worth the challenges. And I’m not talking about the earnings upside from equity (just assume that will be minimal). I’m talking about the upside in experience, in excitement, in building.

Let’s start with the challenges. Then we can get to the good stuff, i.e. what can make it fun and rewarding if you choose the right startup.  Finally we’ll offer our guidance on how to determine if it’s the right startup for you. 

First, if you’re going from a larger much more established sales org to a startup where you’ll be one of the first few hires, there are a few things that you’re going to have to just accept.

Your comp plan won’t be baked, and even if there is an experienced VP of sales at the helm, the org is so new that the plan will likely change as he or she gets a few quarters of learning under the belt.  

Second, remember that world class tech stack that you had at your last startup (you know, the “startup” that had 300 FTEs?)?  Well it ain’t happening here.  Sure they have Salesforce, maybe even Outreach or SalesLoft, but have they invested in ZoomInfo?  Gong?  Will you have to convince them to let you expense Sales Nav?  Be prepared to work through some of the process without a suite of productivity applications. 

Plus, at this stage they won’t have a full time enablement / revenue ops person, so who’s there to evaluate, implement, tie all these tools together, and ensure you’re getting the right ROI out of them. 

Third, how good of a writer are you?  If you’re in a pinch and you need a piece of sales collateral for a key deal, well, you may need to draft it yourself.  If the start-up is selling into the enterprise, you’re going to encounter some RFPs, but you can just hand those over to the solution consultants and ‘quarterback’ your way to a commission check, right?

Think again, you’re not only drafting the RFP responses but formatting, cleaning, Kinkos, etc.

The marketing engine is likely not nearly as refined as your last job.  And by not refined what we mean is they may not have one. 

Wow so why would anyone even consider it?  Well because the experience can be awesome.

You get to be involved in a significant number of decisions that you might not be exposed to otherwise. There are only so many team members on the business side of the house and every smart and reasonable voice counts.

The deals you close make a tremendous impact on the org’s success. If you’re one of 250 AEs, well not so much, but when you’re one of 3 or 4 AEs, every deal is critical to success. This can be hugely motivating.

Yes you will get equity and it might be a bit more than what you’d get at a later stage company, but as we’ve mentioned in a previous post, don’t take the role to get rich from the equity – it likely won’t happen. Just consider it upside and if the business really takes off then great. For more insight into how to value your equity grant, we wrote about it here: “How to Value the Equity Grant in Your Job Offer”.  This is a key topic and so give this a read.

Finally in terms of evaluating sales roles at early stage companies, you likely won’t be able to view a profile on RepVue, and it’s unlikely that someone in your network works (or worked) there given it’s so new. So what’s the most important factor to consider?

Your manager, your leader. What have they done before? What have they built before? You may be reporting to a C level that’s never run sales before, so if that’s the case it’s all about trust. 

Sure they may not know how to design the best comp plan. But do you trust they will treat you fairly?

Sure they may not know all the latest and greatest sales tools out there. But do you trust they will leverage your experience to help guide them.

How strongly do you believe you could follow this person? You can’t really evaluate the history of success, but this person clearly believes in it. Do you also believe in it and more importantly do you believe in him or her?

Spend extra time with that leader during the interviewing and hiring process. Tell them you are going to be putting a lot of faith into them so you want to ensure your values and vision is aligned with theirs.

And if you’re interviewing at a larger b2b or tech sales org, you can get all the info you need via reviewing the RepVue profile for that sales org. To access 100s of these profiles just spend 2 minutes adding a rating to our platform by clicking ‘rate now’ on our home page. We’d love it if you shared your feedback with us too (

Good luck out there.

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