When it comes to building a career, TJ Massie has always been on offense. Even if an earlier chapter of life had him playing a slightly different position. He’s a big thinker, conscientious relationship builder, and calculated risk taker who has a lot to teach us about building trust through relationship selling. Let’s get to it!
TJ was born in Cupertino, the heart of Silicon Valley, long before a spaceship campus occupied its lands. His stroller may have even cruised by Steve Jobs on a local sidewalk. Steve did like his walking 1x1s. The family was out there supporting TJ’s dad who was (and still is) an Internet entrepreneur. But TJ spent most of his childhood growing up locally in Massachusetts after his parents relocated back to Mom’s home turf. Like many Boston area kids, he was on skates early. Hockey was a big part of his childhood and still is to this day. TJ played between the pipes and is a huge Bruins fan. We’ll return to this, it’s relevant. He was a talented goalie and captained many of his teams growing up. As the oldest of four children and the oldest of 20 cousins, he had rigorous early training for a leadership position. That’s a lot of personalities to navigate!
When TJ was fourteen he headed off to Cushing Academy for high school and eventually captained his high school hockey team. He recalls his Cushing experience as really influential. He was exposed to independence early living on campus as a young teenager. Upperclassmen, as they do, helped accelerate that transition. Many of his best friends are from his Cushing days and he still keeps in close touch with them to this day. His parents weren’t too far though and visited pretty much every weekend. We can’t leave that out!
After graduating from high school, TJ spent a year playing junior hockey in Nebraska before heading off to UMass Lowell as one of their goaltender recruits. At Lowell, he met his wife Haley and dual majored in Marketing & Management. It was a great four years where he learned a lot, made close friends, and between his friends & hockey teammates was well prepared for entry into post college life.
TJ left UMass Lowell with the goal of breaking into software sales. Always the competitor, he enjoyed the company of others and was a solutions oriented thinker. A natural fit for a budding sales executive. He caught on with Carbon Black as a member of their first SDR (sales development rep) class. He was referred to the position through a co-worker from his internship and cybersecurity was compelling as a fast growing, emerging industry in 2013. He recalls that he joined just 4 or 5 months before the infamous Target breach happened. Tailwinds come in all shapes and sizes, folks.
Joining a small, fast growing company really helped accelerate TJ’s personal growth path. He was promoted to AE within 8 months by closely following the example of his more experienced enterprise seller teammates who offered training & mentorship. Then another opportunity surfaced. From our conversation I learned that TJ stays ready and pounces when he gets “lucky”.
TJ, even with a relative lack of experience, raised his hand when Carbon Black was looking for a Wisconsin/Iowa territory Enterprise field seller. He landed the role through both his preparation and willingness to move to Wisconsin for 2 years. He built out their local presence in the MidWest and successfully made a “side door” entrance into Enterprise Sales a lot faster than many of his peers. He hit the ground running, willing to do what he needed to do to be successful. “The Go Giver”, a story about giving & creating value recommended by a mentor, drove the development of his personal sales philosophy. TJ hit 200% of his goal each year before eventually returning to Boston for another promotion as a Sales Manager.
TJ reflects upon this rapid rise as “always seeking others advice, that has been super important”. He asked more senior Carbon Black colleagues, leaders in the organization, to meet with him monthly for feedback and to solicit advice. TJ knew these leaders were busy but asked each Carbon Black regional sales director for a timeslot once a month. He asked them “what should I be doing? What should I read? Who’s calls should I listen to?” Then he would diligently follow up on the takeaways from these conversations. “If you’re not on their radar early, you won’t get to the places you need to go. If an opportunity for a promotion or some other career accelerating opportunity presents itself, you need to share your voice and be loud about what you want.” Not rocket science. Just diligent execution.
TJ’s transition back to Boston as a Sales Manager had him managing the Carbon Black Inside Sales team. He created a culture of giving and being a good team player along with hard work. But he aspired to be a regional director of Enterprise Sales like the mentors he had worked hard to cultivate. So after just a year of managing Carbon Black’s Inside Sales team, he stepped down to re-enter Enterprise selling in order to get the experience he’d need to be an Enterprise leader. TJ had the foresight to realize that the people he respected most as leaders had first hand experience of being “in the field”. They knew what their sellers were going through and could give relevant counsel. He was willing to step back, in a way, so that he could step forward more thoughtfully and deliberately later.
His next role brought him to Recorded Future, the “google for cybersecurity”, and he flourished as an Enterprise seller. He owned “named accounts” all up and down the East Coast. After three years of enterprise selling, TJ again made a return to leadership. Recorded Future was acquired by Insight Partners during this time too. He really enjoyed the team there and it was hard to move on but he felt like he couldn’t refuse when leading cybersecurity startup Snyk came calling.
TJ was lucky enough to work with Snyk’s VP of Sales, Brian McDonough, at both Recorded Future and Snyk. TJ joined Snyk managing their East Coast Enterprise sales team from Florida all the way to Toronto. It really helped that he’d worked this territory previously and was able to add value immediately. Brian really sponsored TJ’s growth through their time together and he learned so much from his stewardship. Even when TJ started at Snyk, Brian asked him “so how long until you’re going to go do that VP of Sales job?” He was a great leader who mentored him & included TJ in activities like end of quarter wrap ups, board meeting prep & other leadership activities. Brian was an optimistic sales leader who leaned into the mentality that “thoughts become things”. He had his team set goals, write them down, think them, and believe them. All of this rubbed off on TJ. Brian & the rest of the Snyk team cultivated a special culture but, again, opportunity came knocking.
At this stage of his career he had been fortunate enough to see three commercial orgs built out through an IPO, an acquisition, and one top tier late stage growth ascendence. He felt like he was ready to take the leap and own a team. TJ also surfaced the critical insight that for all of his career moves, he’s never gone somewhere where his boss isn’t someone he already worked with at some point. He keeps track (and close to) good people and makes sure to put his best foot forward to stay in their orbits. It’s not just “knowing people”. It’s going the extra step to connect with people’s personal lives. He prides himself on keeping “customers for life” and that’s how he builds his network. Many customers he’s sold to he counts as some of his really good friends
Through another connection at OpenView he cultivated, TJ first heard about TrustCloud and what Sravish Sridhar & team were building in the compliance, governance & risk space. Snyk had a strong PLG (product led growth) motion so there was some overlap in the GTM motion. Over multiple conversations TJ built his relationship with Sravish who led with honesty & transparency about the company he was building and the kind of leader he was looking for to head up their revenue group. He’d been through the ups & downs as a Founder and his operational experience gave TJ a lot of confidence. More importantly, even with two young ones at home, the Massie family was on board! The final clinching datapoint was a discussion with one of TJ’s mentors who grilled him on the opportunity before realizing that he was an early investor in the company he cautioned TJ to research more fully! It was time to build something from scratch as a first time Head of Sales.
TrustCloud (previously highlighted at the company level) is a distributed software company seeing some really impressive growth. TrustCloud helps companies win business by meeting compliance standards, passing security reviews and managing internal risk. The vision of “assuring trust in every business relationship” resonated with TJ because the whole point of being an effective salesperson is to enable trust throughout the sales process. People buy from people! If you’re putting your best foot forward and enabling trust you’re going to build great rapport and have long lasting relationships.
Today, TJ manages a revenue org of approximately 20 composed of Mid Market sales, SMB sales, the BDR Team, Customer Success, and Sales Engineering. He knows from prior experience to instill in his team the importance of investing in people and each other. He spent his first month getting all of the data in the right places so they could go out and execute at a high level. Now, he makes sure he’s owning the team’s goals and delivering accuracy. “Any good company has a predictable, forecastable business” he tells me. They use Gong to record their sales calls for coaching & feedback. They have dedicated outbound prospecting hours. They do Salesforce hygiene calls and forecast weekly. Operationally, he makes sure he’s meeting consistently with his counterparts across Product, Marketing & Finance. And of course Sravish, TrustCloud’s Founder & CEO, to make sure he’s looped into everything they’re working on. Sales is a team sport and “we’re all in it together” TJ made sure to reiterate. If the company is tackling the same number as a whole it creates great alignment around the whole org and company environment.
In his spare time, TJ loves attending Bruins games as a lifelong fan & player. He brought his 2 year old son to his first game recently and the little guy made it to the 2nd period. Pretty good! TJ goes to a lot of games. But he doesn’t just watch from the bleachers. He’s the emergency goalie for the Bruins. Which means if there’s a goaltending injury, TJ gets suited up and heads to the players bench. Interestingly, the emergency goalie “on call” could also be called to the away team. But TJ assures me that if he got called into action for, say, the Montreal Canadiens he would give his best effort as a competitor and athlete. We’ll just go ahead and trust him at his word. He does work for TrustCloud after all. His favorite neighborhood is the North End and he loves a good Italian meal at Tresca or Bricco. Both, we know, are great!
Here are the insights TJ shared with me that have informed his work and career:
Doing the Work – TJ loves that sales can be for anyone. It fits multiple personalities and there’s a million ways to get a deal done. “If you’re willing to practice the craft and get into a motion to understand the science, trust & human aspect around it you’ll find success in sales. Like hitting a golf ball, you have to do it 10,000 times to get good at it. If you’re willing to put in the work, you’ll be successful”. That sets a lot of people apart! And it’s unique to sales TJ adds.
Make It Known – “If you want to grow in your career, you have to put yourself out there. Be noisy about what you want to do. It comes with performance of course. You have to operate at a high level, achieve your goals & do your job. But don’t be shy to voice what you want.” If people don’t know, they won’t consider you for it. Sometimes when people get frustrated that they’re passed over for a promotion, they never even voiced their goals to their manager. You have to speak it!
Enabling Trust – A lot of people don’t necessarily have trust for salespeople. “Be responsive, be on time, have great follow up, and show that you’re in it for them not just yourself. How can we position what we’re doing together to make this look good for your next promotion? Treat people you’re selling to and working with like they’re on your team, enabling them to be better”.
Don’t Be Afraid to Copy- “I have a lot of great people I’ve learned from. There’s a science to sales but there’s no reason to recreate the wheel either. Keep it simple. Don’t be afraid to plagiarize successful people. Don’t have an ego around that. You don’t need to be a person who changes a path for sellers”
TJ wants to keep growing in his career as a sales leader and hopes to one day serve as a CRO. He’s on the right path and title isn’t the most important thing to him right now. First, he wants to prove he can build collaborative & successful teams. He wants to help grow the TrustCloud business to a successful acquisition or IPO first and help other peoples’ careers flourish like leaders have done for him his whole career. He’s just getting started!
For more about TJ, check him out on LinkedIn or perhaps grabbing dinner in the North End after a Bruins game. When parenting allows! Thanks so much for sharing. Can’t wait to see the impact you’ll make on revenue leaders in the years ahead!
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