November 3, 2021

Creating an Enterprise Account Executive From Scratch: A How-to Recruiting Guide

Jessica Benjamin Headshot
November 3, 2021

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I work at Appcast as an enterprise account executive. I like it quite a lot. The clients, my colleagues, and the tech we sell are all awesome.

Here’s a story about the ways that shared values can translate into business success – even if it all starts with just a low-key gesture of everyday friendliness.

In January of 2021, George Anders, senior editor at large at LinkedIn, approached me via LinkedIn InMail, which is generally a great way to reach me. He messaged me: “I’m in an email thread with a liberal arts grad from Carleton/UChicago (nice person) who has worked a little in recruiting, liked it, and is trying to figure out her next move. Would you have a few minutes to share some insights and perspectives with her? If you’ve got time, that’s great. If calendars are crowded (or you’re just advised-out), I totally understand.”

Being fond of George, liberal arts majors, and anyone who wants to listen to my advice about anything, of course I said yes, I’d love to speak to her.

I think most of us, whether we work in talent acquisition or not, realize it’s hard to hire people right now. But then, it’s always been tough to hire good salespeople. I’ve recruited a lot of people, women in particular, for sales over the years. When I meet another woman who thinks she might be interested in sales, I encourage them because I think it’s a great career for women.

I had a look at Vaishali Umrikar’s LinkedIn profile. I noticed that she was the founder and CEO of The Empowerment Bag, which I thought was incredibly cool. So Vaishali and I set up some time to speak on the phone. Then we had some insightful and long talks. I talked about what I did as a sales executive, and Vaishali told me about her experiences as a recruiter. We talked about how much love we share for the small liberal arts colleges we were fortunate enough to attend.

I did a bit of recruiting to make money while in law school and think of recruiting as sales. You make two sales, one to the client to use you in the first place and one to the candidate who you need to sell on the opportunity.

So, at some point during our hours of talking, I realized that if Vaishali could get me to spend that long talking to her, that future clients would probably like talking to her, too. I asked if she might be interested in learning how to do what I do, and she was. It was great.

Not being a hiring manager myself, my next “pitch” was to our VP of sales. He liked her, but he wasn’t sure if enterprise sales was the right fit. I’m a big fan of culture adds rather than culture fits, so I convinced him that an enterprise sale isn’t something magic; it’s just a big, complex sale. And I thought anyone who enjoyed sales and who was supersmart could figure it out.

Fast forward to Vaishali working at Appcast. I was assigned to be her buddy. Our buddy system at Appcast is excellent. I had two buddies when I started. Susan Oxford, Appcast’s VP, talent acquisition, paired me with one sales buddy, Jon Simoni, and one culture buddy, Karel Prickett. Since I was hired remotely during the pandemic, having these two guys to talk to was extremely helpful. They both had good advice and helped me integrate into the company more smoothly. They both sell so much they give me stretch goals to aspire to and inspire me.

I’ve loved being Vaishali’s buddy because she’s both intelligent and cares about Appcast. We exchange best practices, and she sits in on some of my meetings. I don’t know how much I’ve taught her, but I sincerely enjoyed talking to her and look forward to our calls. Everyone needs a buddy, especially when starting a new job and working from home during the pandemic.

Although she did all the work herself, I feel a little pride as she hits each milestone, like when she got assigned a sales development representative (SDR.) That was big because it gives her additional leads and frees her up to sell more. I taught her how to work with her SDR by inviting her on a call with mine. My SDR is, himself, amazing. So we explained how we work in a successful partnership to tackle prospects.

My advice to her for working with an SDR is good, general advice for colleagues. The goal is to find out how that person defines success and to help them reach it. I’ve had two SDRs at Appcast. The first one, Tom Kinnie, wanted to be an enterprise account executive, so he used to sit in on most of my prospective client pitches. It was nice to have some company, and I enjoyed showing him some of my strategies, knowing he would soon move on and build upon them. He now sells more than I do. I’m super proud of him, although I had little to do with it.

My current SDR, Jeremy Pineo, is a single dad who doesn’t want the relationship maintenance that comes with my job. He’s happy where he is. I’ve always been impressed that he knew what he wanted with his career. He writes very strategic emails and is the primary user of Outreach for our team of two. I rely more on LinkedIn, social selling, and referrals. That combo has gotten us some great meetings. He knows me well enough to know I care about diversity recruiting and helping our clients do it. He knows how to sell meetings with me to prospects. And that’s why he’s one of the best SDRs I’ve encountered.

Vaishali’s doing great, and I’m enjoying watching her career develop. I think I’ll know I did my job when she outsells me. I’m excited about that day.

Coincidentally she just bought her first house, and I sent her a Money Tree. I think between her brainy determination and charm, she won’t need a tree to succeed. She will have done it for herself, much like I did at her age.

These are my takeaways for recruiting and hiring salespeople:

1.      Pay attention to people you meet. If they’re persuasive and you enjoy talking to them, they might have a future in professional sales.

2.      You may have to advocate for the person you recommend internally as well. You can probably do it if you’re persuasive as well.

3.      Upskilling and reskilling are secret weapons in talent acquisition. Many skills are transferable.

4.      Be open to having authentic talks with people you encounter. You never know what might come of it.

5.      If you want your employees to bring you good referrals, have a good referral program. I donated the bonus I got for recruiting Vaishali. I now consider her a friend, and keeping the money seemed unnecessary. We both win working together, as does Appcast.

Jessica Benjamin is an enterprise account executive at Appcast. Follow her on Twitter at JLBHireCalling.

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