How can I, a 35 year old sales professional and small business owner, find a job at a startup?

I currently own a successful retail business that I started 2 years ago. The business is fairly hands-off now and I have decided to put myself back in market for a startup sales role. Prior to my business, I worked as a Biz Dev Dir. at a failed startup and before that as an Account Exec for a software comp selling enterprise software solutions successfully. I've interviewed with many startups. For some I know the fit is not right, but for others I'm not sure what I'm doing wrong. Any advise or guidance would be immensely awesome.


It's great that you have a ton of experience in sales and business growth, and this will likely boost your credibility in many ways. However, startups are often looking to hire folks who can be extremely agile and switch to a new strategy as soon as they learn that the current one isn't working.

I'd be careful, in communicating your background and deep experience in the industry, that you don't go saying something like, "I know exactly what tactics will and won't work," (because at a startup, you really don't know til you try) but rather, "Because I've done sales at companies of different sizes, in different industries, some of which have failed and some of which have succeeded, I know how to quickly identify when a given sales approach is or isn't working, and shift to a new approach to better target that particular audience and increase close rates." Give examples. Talk about deals you've saved, times you've had to change your approach.

Also, chances are - if you're joining an early-stage startup, you'll play a key role in helping define their sales strategy as the company grows. Have you done this before? Talk about how you've approached this at other companies.

Hope this gives you a better framework for thinking about how to communicate your value. Best of luck!

Answered 7 years ago

I'd be happy to do a mock interview with you on a call and give you feedback. We could do a preliminary session where we focus on the types of positions you want with what types of companies then I could do mock interviews with you and help you put together your resume, your narrative, and your presentation. I've hired a lot of startup employees and contractors and advised dozens of companies on building their teams. There's definitely a cultural element and it also depends on what market you are in. For example, I run startups in Nashville. That's not SV which is not NY. There are nuanced approaches and preparation you need to do for each market.

Answered 7 years ago

Figure out your values. What do you want to promote?

Make a list of startups. Screen them by values.

Contact those who share your values. Now you have a Why. Every organization can make room for someone who has a plan to make money for them. Do you have a plan? Have you shown it to employers? Or have you simply said you will "show up for a sales job"? (I honestly don't know.)

Aim for interviews at startups where a position is NOT advertised. Competing with a zillion other candidates is not what you want to do. You can also get a custom-made role this way.

Why the startup attraction, anyway? They're risking hugely on you...and any salesperson they hire. Unless they have deep funding pockets, your salary is a bet.

Instead, a 20-30 person company is much more used to hiring "one more person". Are you wanting to build the sales department? Have you discussed this with employers? (Some will be attracted, some indifferent and some scared off by you not wanting to be a worker bee if that is the case. Be ready for that.)

Were you the only salesperson at the failed startup you had experience with? Don't associate yourself with failure. Either get a good experience to talk about that came from it, or ditch it.

Answered 7 years ago

It's really good that you are putting yourself out there and interviewing. I would suggest you start reaching out to different start up peeps for coffee. You can learn a lot about an industry or venture over casual coffee conversations.

I came across two sales roles in my past at startups by getting out there and meeting people.

Reach out if you want to chat more about this.

Answered 7 years ago

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Answered 6 years ago

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