Over the past decade, Jeff McDonough has been part of two of the biggest success stories in Boston Tech. He joined Seismic Software when they were at <$100k in revenue and built a global team as they scaled to $100M+. He then started a consulting firm that helped grow Klaviyo into a household name as they scaled to an eventual IPO. He now leads the East Coast sales team at Mindtickle, which is positioned to redefine the sales enablement category.
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 have two older brothers that I idolize. Both have been in the tech space and performed as individual contributors who then grew into leadership roles. Whatever profession they got into, that was going to be my path. It's funny because our father was in procurement for 40 years, so he must think we’re all sellouts. Truthfully, I really never felt like a salesperson. I always look at my career as being a problem solver that is fortunate to be the least intelligent person in the room.
You climbed the corporate ladder from AE to VP of Sales in 10 years. For all the AEs reading, what does it take to make it to VP of Sales? How’d you make it there so quickly?
A combination of things:
1. Being in the right place at the right time. Joining a growing business with leadership willing to invest in you gives you the best chance to grow and have an opportunity to lead.
2. Check your ego at the door. If you want to be a leader, you have to have a team-first mentality. Everyone thinks they want to be the VP of Sales, but very few are built for this type of role long-term.
3. Focus on building a great team — always be recruiting and looking to add A-players to the team. If you can continue to up the level of talent that comes through the door, it keeps the team sharp and competition high. If you’re an AE, refer the most competitive people into the business and then outwork them.
You’ve been selling tech nearly your entire career. How has the B2B tech sales landscape changed since you started 10 years ago?
10 years ago, you could find a person or two at a company, tell a great story, and get a deal done. Now, you need to get executives involved early… multi-thread to buying committees (we sell large enterprise deals so on average 8+ people) and build a bulletproof business case.
The thing that will never change is naturally curious sellers — willing to outwork your opponent will always win.
You currently sell sales tech, so you’re talking to sales leaders daily. What’s one thing that you see sales teams struggle with when it comes to purchasing, implementing, and seeing ROI from investments in new tools?
There is serious tech fatigue. Everyone has spent the last 10 years buying best in breed tech that solves a problem at a point in time. This is an expensive and siloed approach. Companies end up with bloated spend on tech and sellers end up with a large tech stack that takes significant time to navigate. Therefore, they don't leverage tech to the best of its ability. In 2024, sales leaders want to consolidate their tech stack, save money in year one and be able to point to clear ROI in years 2+3. That's the biggest reason I joined Mindtickle, we do exactly that — we are a CRO’s dream.
What does a typical work day look like for you? Walk us through it.
If I could detail this out, I wouldn't love my job or be very good at it. Every day is different, that's why we sign up for this line of work. Revenue is always top of mind but finding talent, retaining talent, talking to customers takes up a majority of my time. My ideal day is 50% with my team and 50% talking strategy with customers.
What's the one thing you’ve found that helps you be successful in sales?
LISTENING. There is always a solution. It's those who listen and are willing to put in the work that succeed. Also, put yourself in the shoes of whoever you are talking to, that goes for internal and external conversations.
What are your long term career goals? Early retirement or future CRO?
My long term goals are to make an impact on the people around me. Control what I can and be present in any role I take on… personal and professional. Ideally, I would like to be coaching my daughter Melody McDonough in 10 years and carry her bag on the LPGA tour one day.
What’s your favorite sales movie?
Tommy Boy. Every seller stumbles a bit trying to find their style, voice and superpower. Jeffy want Wingy.
