Sales Advice from a GTM Genius

Yoooo, happy Sunday folks! It’s been a long week. I hope the sales have been fast and furious for y’all! I’m relaunching this newsletter by focusing on interviews with really cool and insightful people in the sales world. Today is my launch day, and one of my good friends (and all around cool people) agreed to be the first guest.

Also the most frustrating part of Docusigns were when the client would take a little….little bit too long to sign it. Waiting. Refreshing my email. It was, lets just say fun.

Okay, but enough about me. Now its time for what you came for. My 1 on 1 with my good friend and GTM (Go To Market) genius, Benyamin Holley. I’m like 75% I know what an MSP is too, but I’ll let him explain it.

Okay and now for Ben’s Divine 9 Sales Q/A:

1.) Why sales? What got you into sales? And can you briefly describe your career history?

I got into sales because I needed a job. Pretty cliche right? I applied to work at a motorcycle dealership that I’d bought a motorcycle at a few years prior.

I worked in a lot of shitty dead end jobs from 18-26, where I got into my first startup, a music education SaaS. I had also run my own recording studio during that period.

Once I got into the motorcycle business it was a wrap, I loved selling. I got into SaaS sales after the motorcycle dealership, and have been in it ever since.

2.) Would you rather work at a big company? Medium sized? And or startup? And why.

As small a startup as possible. I’ll probably start my own company one day. I know I can raise money and recruit. When you’re at a small company you can invent the world you want to live in and you’re not constrained by all the mistakes your predecessors made. 

Plus, a startup is basically a religion and I’ve always wanted to start a cult. 

3.) Who is your ICP now? And how do you best reach them? What have you tried? What did not/does not work well?

MSPs, which are outsourced IT firms. Best way to reach them is in person, at conferences. I would say they like cold outreach less than most. I’ve tried a lot of stuff that pushes the envelope that they haven’t really liked - email me at [email protected] if you want more details 🤣. They still respond to cold calls and emails if you’re polite. 

Their preferred avenue is network/trade shows, which isn’t really scalable. But you need to create raving fans since the community is so small. 

4.) What are your thoughts on territory mapping? How do you set that up? And how do you effectively comb through your territory?

I wouldn’t work somewhere with territories. Sorry lol. My territory at all 3 SaaS companies I’ve worked at has been the whole world. I would rank accounts based on a simple criteria like revenue and employees, or locations. Probably not a good way to do it honestly, but I haven’t had the time to operationalize a better way since I started at Cyft, but I certainly will soon. 

5.) What is your cadence/outreach like? What have you found to be most effective?

Segment phone and emails campaigns. Have them totally separate. I run email campaigns in smartlead and make calls in my dialer. Ne’er the twain shall meet. That’s by design for a lot of reasons I can’t get into here.

All I can say is you need to blast the cannons. Never stop the cannons from blasting. Right now I’m not doing much cold calling since I’ve been focused on fundraising, but we were sending maybe 100-200 emails per day to VCs and booking hella meetings.

Remember that pipeline solves all problems in a business. Not even exaggerating. 

6.) What do you like to do outside of work?

Motorcycles, video games, reading, hiking, hanging with my hairless dog. More work. AI coding. Reading. I’m reading like 5 books right now - no joke. It’s too many honestly. 

7.) Where do you think more sales reps these days should focus their time and energy outside of making dials/sending emails? What should we be learning about? 

Learn how to code with AI. Dead serious. We all need to learn how to use AI. You really are going to get left behind if you don’t know how to use it. Doesn’t negate the human element from any of our work but if we’re in SaaS we need those technical chops to be able to connect to our buyers. 

I would also study marketing and copywriting. Read books from exited startup founders. Don’t just pigeonhole yourself as a sales rep. You are a business person and need to treat yourself like one. Too many reps are too myopic about their career identity and I think it hurts and limits them. 

Right now I’m trying to learn about finance, ABM and recruiting. 

8.) What makes a salesperson successful in your mind? Who are other salespeople that you follow/others should follow too?

Integrity, honesty, thoughtfulness. All things that I have lacked at one time or another than has made me much worse at my job. A ruthless disqualification process. Josh Gillespie from Pandadoc told me we are “in the business of disqualification”. It’s always stuck with me. He’s so right.

Guys I follow religiously:

• Eric Nowoslawski

• Kellen Casebeer

• Vaibhav Namburi 

• Scott Martinis

• Jesse Oulette

9.) Lastly - what does success mean to you in your career? What is your end goal?

Success for me is about two things: 

• Achieving escape velocity from a big exit 

• And waking people up to their own potential and deep esoteric truth in the process

My career is about money, but if as a byproduct of that I can help people get redpilled about life, work, AI, God or anything else I’ll do my best to do that. 

My current boss James has asked me some really interesting questions about why I want Cyft to exist and what’s in it for me. I told him I want to give people a sense of what’s possible that they hadn’t previously considered.

If I can do all that, and provide for my family without screwing anyone over, and maybe get a big exit and dick around in a camper for a year, then it’s a win. 

^Big S/O to my buddy and GTM expert Benyamin here. If you want to follow Ben (you should), hit him up on his socials - LI and Twitter/X.

Until next time you sales psychos, lets have a day!

-Kevin