This is our interview with Jake Shaffren, Director of Sales at DiscoverOrg. You can follow DiscoverOrg at @DiscoverOrg.
Sales Assembly: Give us your quick background in sales.
Jake: I guess you could say I was destined to be in sales. When I was a kid, I put a Lego under my pillow to try and hustle the tooth fairy. Then, my Dad and I would negotiate over the the price per tooth...I then "graduated" to selling pizza and grilled cheeses at music festivals and concerts to support my travel expenses and ticket fees for the next show.
I stumbled into my first SDR role - had no idea what I was getting into. I was good at it, really good at it. I loved the hustle and the chase. So much so my first company sent me to Australia to build an SDR function.
Then, I found DiscoverOrg. I came in as SDR #3. A couple of years later, I was running a department of 55 SDRs across several teams and several offices.
Sales Assembly: What's your biggest accomplishment in sales or sales leadership?
Jake: It was actually recently. Scaling the team from 3 to 50+ was for sure an awesome accomplishment and to be given that responsibility and trust is certainly something I don't take lightly.
A couple of months ago, one of our top SDRs got promoted to an AE role, and during his time as an SDR, he supported me 1:1 as I transitioned to a closing role. Helping him close his first deal from start to finish, watching him go through the negotiation and ultimately hitting the gong was humbling in a lot of ways. To see it come full circle and know that I had a hand in his success was really rewarding.
Sales Assembly: What's the best piece of sales advice you ever got?
Jake: Our CRO, Patrick Purvis, said to me when I first started with DORG, "Everything interesting in sales happens in the grey area. The white area is safe and comfortable, you're going through the motions and passively taking orders, not selling. If you've gone into the black you've pushed too hard and are never going to win. Frankly, you've probably pissed someone off along the way. It's the balancing act of going just far enough to reframe someone's thought process and get them from point A to point B. It's turning a no into a yes. That's selling, and that's when it's the most fun."
Sales Assembly: What's the biggest challenge facing a sales rep today, and how would you recommend they overcome it?
Jake: I'll borrow a Steve Hay's line here - it's the "Sea of Sameness." Everyone is doing or saying the same thing, and now, with the email cadence tools, anyone can send hundreds of emails at once. Find a way to stand out, make yourself unique. I get tons of emails - countless in a day. I ignore most. Same with In-mails now. Most times, I ignore them. You know what I don't get tons of? Phone calls. Don't hide behind email or social channels. Pick up the damn phone, it's your best friend in sales.
Sales Assembly: Do you currently have a mentor when it comes to sales, or have you ever? If so, what did they teach you?
Jake: Too many to name. I'm really fortunate at DiscoverOrg to be surrounded by incredible talent. It's humbling frankly. Dave Sill stands out - our Head of Sales Enablement. He looks at sales like an art form, and he focuses on the psychological elements (e.g., the art of story telling, how to master persuasion). Chris Hays too - our COO. He's a wizard when it comes to all things technology, and his business acumen is equally as sharp. He can look at a problem, understand the core reason it's a problem - picture first, then implement the mechanics to fix it, and at the end, the result is 10x better than before.
Sales Assembly: What's the best sales book you've ever read? What are you reading now?
Jake: That's tough. There are the classics: How to Make Friends and Influence People and Fanatical Prospecting are always on my desk. The Challenger Sale is an all time favorite. Currently, I'm reading Never Split the Difference by Chris Voss. Highly recommended.
Sales Assembly: Best sales or business related articles, podcasts or newsletters?
Jake: Sales Assembly obviously. The blog that Gong.io puts out is awesome. They use real data for their analysis and make empirically driven conclusions. Always a fan of Michael Pedone and what he publishes. Sales Dev podcast with David Delaney. I think the best resource though is the Modern Sales Pro forum. Really educational and I've learned tons from reading through those threads over the years.
Sales Assembly: What's the best advice you'd give to someone just starting a career in sales?
Jake: Be tenacious. The harder you work, the more money you'll make. It's that simple. Bust your ass and learn as much as you possibly can. Absorb everything. Break shit...can I say that? Seriously though, this is a constantly evolving profession. What works today won't work tomorrow. Break the rules, find new ways. Screw the status quo, try new things. You'll fail sometimes - who cares. Keep trying and pushing to get better and expand your comfort zone.
Sales Assembly: Do you see any interesting future trends as it pertains to sales?
Jake: I think we're automating ourselves to death. There's most definitely tons of power in AI and Machine Learning and what that means for the next generation of sales. Yes, you can do some incredibly powerful things with all the sales tech out there. Sales isn't an assembly line though, nor do I think it ever will be. There's still a human element. Learn to talk to people and SELL them. You can invest in all the fancy widgets in the world, though if you don't know how to actually sell, they won't solve your problems.
Sales Assembly: What's the one tool in your sales tech stack you couldn't live without?
Jake: Two answers here. The phone - does that count? I'd always rather have a conversation with someone on the phone rather than a long email thread. You can learn so much more from a live conversation - the pauses, the tone of voice, etc.
The second - and yeah, this is biased though true. A good data provider. It's the foundation to everything else. Period. You can invest in the most robust engine in the world, but if you're not giving it gas or changing the oil on a regular basis its going nowhere fast. Think of it like this: what good is a power dialer, if all the phone numbers are junk?