Inside Drift: Meet Jason Richman, Sr. Strategic Revenue Acceleration Executive, Enterprise

Today we’re introducing you to yet another member of the Drift team.

I know you’ve already met Shannon Donovan, Mary Mitchell, Catherine LaMacchia, Nadine Shaalan, Kahlil Trocmé, Britnee Laughlin, Sam Boyd, Allison Betito, Carolina Caprile, Michelle Ai, Frank Schepps, Tate KnappAlexa Nguyen, Zareena Javed, and Chrissie Cronin.

This time I’d like to introduce you to Jason Richman, Sr. Strategic Revenue Acceleration Executive on our Enterprise team. Jason was among the first 100 employees at Drift and has witnessed first-hand the hypergrowth that Drift has experienced over the past few years. He is passionate about helping to create the best possible digital experience for our customers’ customers and finding solutions for our enterprise clients. He is also the proud father of three kids under the age of 6, and since Drift went Digital First, he has been able to play with his kids in the morning and have family dinners after he signs off for the day.

Ready to meet Jason? Let’s go ⚡

Editor’s note: The following has been edited and condensed for clarity.

Kaitlyn Martins: First thing’s first – can you tell me a little bit about what you do at Drift?

Jason Richman: For sure, so essentially I advise enterprises on how they can digitally transform their website experience to accelerate revenue. Most enterprise B2B companies have legacy processes in place to engage site visitors, force prospective customers down a pre-defined marketing funnel, and then wait…in some cases days or weeks to get followed up with lead scoring, routing, and manual sales rep follow-up. This approach may have worked five (or more) years ago, but it doesn’t cut it in 2021 – especially with the pandemic accelerating digital transformations. How can B2B enterprises pivot from being “company-centric” to truly delivering “customer-centric” digital experiences? That’s what I do at Drift.

Kaitlyn: What does your day-to-day typically look like?

Jason: My day-to-day typically includes advising current enterprise customers on executing best practices with Drift, and challenging and educating future Drift enterprise customers on the merits of adopting revenue acceleration to meet their buyers where they are, on their terms.

Kaitlyn: Now that we are a Digital First company, how has your routine changed?

Jason: I have three children all under the age of 6 years old, so Digital First has been an absolute game-changer for me personally. I drive my oldest son to school in the mornings, read to my children before our nanny arrives, and then am heads-down on work for the next eight hours. When I do have time in between meetings, I’m able to squeeze in a quick workout. Lastly and most important to me, I’m home every single night to eat dinner with my family – not something I was able to do with the commute home before we went Digital First.

Kaitlyn: How is your team structured and how do you share roles and responsibilities?

Jason: At Drift, we’re all about team selling, so our teams are architected to optimize for that approach. We have a 2:1 SDR to AE relationship. There are 4-5 enterprise AEs per team, led by a Director of Sales (player/coaches that tag-team pursuits with AEs). Directors of Sales roll up to our SVP of Sales, Josh Pennino. He’s arguably the best sales leader I’ve come across – he actually dives into the trenches, meets with frontline AEs 1:1 on a regular basis, and has a 360-degree view of all the levers/angles we should pursue when partnering with future customers. Josh reports to our CRO, Todd Barnett, who has completely changed the trajectory of our business since joining.

Kaitlyn: Why is now an exciting time to join the sales team at Drift?

Jason: The enterprise market is ripe for revenue acceleration. Legacy industries have accelerated their digital transformations from what was on a 5-10 year roadmap, to now needing to digitally transform in 1-2 quarters. Its very rewarding to have a meaningful impact on large enterprises’ growth trajectories and creating better digital experiences for our customers’ customers.

Drift is a very collaborative scale-up. Personally, I think it’s exciting to be able to give constructive feedback to sales, product, marketing, customer success, and actually see that feedback get executed. Many businesses have silos across different teams and departments, but Drift is truly a collaborative business that seeks feedback (not consensus) to improve and grow.

Kaitlyn: You’ve held a couple different roles since you started at Drift, how would you say you have developed professionally in your Drift tenure (so far)?

Jason: Yes, that’s putting it lightly! I joined Drift as a Director of Sales back in January of 2018 as employee #73. At first, I managed a team of eight reps. We were very much a transactional business at that point. By the end of 2018, I managed 16 reps and led the re-launch of our mid-market team. In 2019, I led the day-to-day management of one of our most strategic partners and helped launch Drift’s first official international team. In 2020, I decided I wanted to spend my time doing what I’m most passionate about…selling. So I went “back into the funnel” as an Enterprise AE. It’s definitely been a non-linear career path at Drift, but the leadership team has been fully supportive along my journey.

As for my professional development, three things really stand out:

  1. My public speaking has improved significantly
  2. My ability to lead a hypergrowth sales team
  3. My coachability (both giving AND receiving coaching)

We are now at 445 employees and just closed out a record-breaking year of growth and market expansion. Drift is truly a rocketship, grab a seat 🚀

Kaitlyn: What’s a fun fact that people might not know about you?

Jason: I met the Dalai Lama while studying abroad in New Zealand. That was a surreal experience.

Kaitlyn: Have you picked up any hobbies or discovered any hidden talents since we went remote?

Jason: Yes, patience! I’ve never been the most patient individual, but working remotely has forced me to focus on quality inputs (personally and professionally) and know that those quality inputs will pay dividends in the future.

Kaitlyn: Finally, what advice do you have for prospective Drift candidates?

Jason: Be your genuine self. At Drift, everyone is welcomed and we value diverse perspectives.

For candidates, do your due diligence. There’s a ton of inbound interest for candidates to join Drift, so make sure you’ve done your homework on Drift and revenue acceleration prior to your interviews. My two least favorite questions I got asked when I was a hiring manager were, “So, how long have you been at Drift?” and “So, what do you do at Drift?”

Authenticity and preparation are the keys to success interviewing at Drift (and anywhere your career takes you).

Want to work with Jason? We’re hiring. Check out our open roles here.

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