Canopy Connect’s Stary is Supercharging Sales via His Deep Finance and Tech Experience
I had the pleasure of interviewing Corey Stary, who is the Head of Enterprise Sales & Partnerships at Canopy Connect. Canopy Connect is a new entrant into the burgeoning InsurTech space. Best-known as the “Plaid of insurance data,” Canopy works with a variety of FinTechs, marketplaces, and lenders to allow consumers to use their insurance policy details to achieve positive financial outcomes.
Before joining Canopy, Corey was a founding member of the Enterprise Sales team at Clearbit, a buzzy, San Francisco-based MarTech, where he spent three years. Before Clearbit, Corey worked in pre- and post-sale roles at several other Enterprise-focused SaaS companies in the Bay Area and New York City.
Corey transitioned into SaaS after an early career in financial services and is an alumnus of Merrill Lynch and Prudential Asset Management.
Thank you so much for joining us!
How did you break into a career in tech sales?
I was always interested in tech and started designing websites in high school, a hobby I continued into college and beyond. I graduated from college in 2008 — before SaaS sales was what it is today, and also a challenging time in the global economy. I didn’t see myself coding as a long-term career, nor were my skills of the caliber required for most software engineering roles. I didn’t think there was a place for me in tech.
I chose the “safe” route initially; landing roles at big brokerages who offered stable — if not particularly exciting — work. I kept a pulse on the tech/SaaS scene by going to networking events, volunteering for a Techstars program, and doing free work for young startups to build up my experience.
I eventually leveraged that exposure to secure a role at an established FinTech. When an opportunity to join a hyper-growth startup came my way via a professional connection I’d met through Techstars, I hopped aboard and never looked back.
What has been your biggest challenge in your sales career?
100% it was landing my first Account Executive role coming from a non-standard background. I wasn’t the guy who joined a sexy, fast-growing startup as an SDR out of college and then got a promotion to AE 1–2 years later.
Instead, I was the guy who invested a lot in cutting my teeth in finance (including getting several licenses that I later had to give up), then switched industries, and then switched functions within my new industry.
My first role in SaaS was in CS. I was at a FinTech company that sold to big banks and asset managers, and it wasn’t unusual for the CSMs there to be sourced from financial services firms, which is what happened to me. But once I was in CS, hiring managers — externally and internally — wouldn’t consider me for AE opportunities.
I kept pushing. A few companies and some years later, I eventually got an internal promotion that brought me from post- to pre-sale.
What is it that most excites you about sales?
Impact. I’m motivated knowing that my work (and my team’s work!) has a really tangible, measurable impact on our business and our customers’ businesses in the form of new revenue and unlocked ROI, respectively. It’s not simply sitting down at a laptop from 9–5 and writing emails and taking Zoom calls. Especially at an early stage company, it’s a lot of learning/listening, planting and replanting seeds, creatively nurturing, and iterating as you grow.
If you had to share “words of wisdom” with a new Sales Rep who’s about to start their career, what would they be?
I think sales gets a bit of a bad wrap sometimes, especially among early-career folks in SDR roles. There’s a perception that sales involves jamming products down customers’ throats, that it’s a job you do until you get the opportunity to go elsewhere more desirable (Product, Marketing, RevOps, etc.), and that it’s meant for one type of person: the uber-alpha “tech bro/sis.”
None of that is true.
If you feel like you’re jamming a product down someone’s throat, you’re selling the wrong thing at the wrong company. As a seller, your job is to work hand-in-hand with your customers to determine if there’s a mutual fit or not (and if there isn’t, that’s okay!).
While some folks do choose to transition out of sales, plenty don’t! By having a job in sales, you’re lucky enough to have a career that scales nearly infinitely as you grow. You can progress from high-volume, low-ACV transactional selling to low-volume, high-ACV solution selling. Or from SMB customers to Enterprise ones. Or from simple products to highly-technical ones. From IC to manager, and so on.
Lastly, there’s no one-size-fits-all sales persona. It’s up to each seller to find his/her style and voice. Two reps with totally different approaches can be equally successful. Yes, sales is partially a science (mastering best practices always helps), but it’s also an art, with plenty of opportunity for creativity and judgment.
How can our readers follow you on social media?
LinkedIn is the best option! Find me at: https://www.linkedin.com/in/coreystary/
This was very insightful. Thank you so much for joining us!
