An interview with Jay Staler, a fly fishing instructor turned technology Account Executive

Jay Staler is a Channel Sales Account Manager at RingCentral. He’s also a former fly fishing instructor and former real estate agent, both of which have translated well to his current role. We talked to Jay about his background, about selling to salespeople, and what fly fishing can teach people about sales.    

You’ve been selling your entire career (over a decade). How did you get your start in sales? When did you know it would be your career? 

I’m a 3rd Generation Salesperson. Both of my grandfathers, as well as both of my parents were successful salespeople and are now small business owners. The sales-intangibles are very much ingrained in my blood, and I take a lot of pride in continuing that tradition! After seeing their success and my similarities to them, I knew before college I would go into sales, which led to pursuing the study of things I was interested in, history and journalism, rather than something more “business” focused. 

My foray into entry-level sales was as a recruiter for an IT Staffing firm. From there, I received my real estate license and worked for a large homebuilder. My mom was a broker/owner of a REMAX Office at the time, so she was a mentor for me and helped me navigate many complicated deals. Whatever success I’ve experienced later came from those first two jobs. I eventually grew tired of B2C, working nights and weekends, so the real estate experience and a connection at Zillow helped make the jump across the country to Colorado and into tech. Best decision I ever made. 

You used to be a fly fishing instructor. Fishing (especially fly fishing) requires a lot of patience and trial and error. Are there any parallels from your time teaching fly fishing that carry over into sales? 

There are a TON of parallels between Fly fishing and sales — landing more prospects / fish means putting more hooks / communication in the water; you’ll have good days and bad days, even when you do everything perfectly; losing that whale right before it gets to the net or gets marked closed/won. My favorite would be that sometimes the fish aren’t liking your presentation or type of fly — they just aren’t buying what you’re selling. The fisherman or salesperson who only has 2 or 3 ways to fish or to sell will hit a low ceiling quickly, and will likely stay there. 

You sell sales tech, which means salespeople are your target market. What’s it like being a salesperson selling to other salespeople? Is it easier or harder? Do they tend to see through your sales tactics? How do you adapt? 

We actually sell to all manner of buyers, from IT directors, customer service managers, executives, so it’s not exactly sales tech, but I do LOVE selling to salespeople. I find it refreshing because there’s no hiding behind your “Account Executive” title. We all know each other’s motivations. I love to connect with my buyers, and selling to salespeople makes that incredibly easy. We’re all in the same boat and there’s a mutual understanding. I believe they want to see that you’re prepared, competent, trustworthy, and have at least made an effort to establish rapport. Being genuinely curious about how their sales team is performing can open up a lot of doors for pain-points or areas that can be improved by my product. They want you to ask for the business and have a great reason why. Storytelling is a favorite method of mine, and I love to make value adds like “I wish I would have had this when I was selling real estate, or recruiting, or making a ton of cold calls every day - it would have made me better at my job”.  Salespeople value a high-level of transparency and humanizing the conversation, and if you give them anything less, they’ll dump you quickly. I would. 

What does a typical work day look like for you? Walk us through it. 

My job is to sell UCaaS through a network of partners or resellers, and make sure they are happy and motivated to sell our solution. It’s essentially account management but for new business, if that makes sense. I handle product demos, quote and contract preparation, play “calendar tetris” when trying to align with the many product specialists/engineers for more technical demos, run trial accounts/POC’s, discuss new products or training with partners, and do plenty of sales follow-up. If you manage your partner relationships properly, it’s a great feeling when it starts to pay off for everyone.

What advice would you give to someone who is just starting out and wants to be successful in sales? 

Get-in-where-you-fit in! Your first, second, or even third sales job likely won’t be your forever gig, but it’s where you’ll find and develop your strengths, and you’ll need to lean into those strengths later. You don’t need THE sales job, you need A sales job. Some people are better farmers, some are better hunters, some aren’t cut out for it at all, but at least you’ll know. The best are the best at the basics, and you’ll want to master Sales 101 before moving on. Be a sponge for training, read every sales book and listen to every podcast possible. Talk to the veterans in your organization. Most of all, identify any mentor/mentee opportunities. Being pushed or encouraged by a mentor that can identify the gaps in your skillset and help you improve them is huge. Find someone that will help you get from a 5 to a 7, and then from a 7 to a 10. Lastly, be prepared to ride the wave. You’ll have good times and you’ll have bad times. I’ve experienced plenty of both and will continue to experience plenty of both. But being consistent and resetting your mindset daily will carry you through. Some of the best advice I ever received was “Ya just gotta close on somethin’, man!” Whether it’s closing on setting the appointment, receiving positive feedback on your demo, or having someone return your call. When the going gets tough, focusing on small wins will carry you through until you get that big order. 

What are your long term career goals? Early retirement or future CRO? 

I think we’re taught to be enterprising, especially in sales, and that the only measure of success is seeing the development from BDR to AE, Manager, Director, VP, SVP, and so forth. This is all valid, but you never know who’ll you meet along the way and what doors will open for you. For now, I’m focused on being the best AE I can possibly be in good times or bad, and will be ready to make a change when that time comes. I love being a salesperson and I know I’ll want to be connected to the profession forever, in whatever form or fashion. I’ve considered sales training or enablement, but I think I’d miss the thrill of the chase and that feeling when that big order that you’ve spent so much time on comes in. With that being said, it only takes one order, connection, or account to get that early retirement! 

What is your favorite sales movie? 

You see this watch? This watch cost more than your CAR!!! Always. Be. Closing. As a former real estate agent I was always able to connect with Glengarry Glen Ross and it’s a favorite of mine as well as both of my parents. 

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