Sales Strategy and Operations with Matt Montsinger

Other Roles

Matt began his career with EY, splitting his time between the Audit and M&A groups. After two years, he pivoted to a sales strategy role within Gartner. Matt provides added background on his current role and how public accounting helped him get there.


  • Audit to Strategy & Operations
  • Climbing the corporate ladder
  • Importance of good managers
  • Routine vs. project-based work

Matt, thanks for joining. Can you tell us about your career background? 

I grew up in Memphis, Tennessee and went to Southern Methodist (SMU) for college where I studied both Spanish and Accounting. I can’t say that accounting was a passion of mine, but it had a 100% job placement at the time, and I remember turning to my dad during a job placement meeting and him saying “there you go”.
I interned with Ernst & Young’s audit practice during my senior year. I was on the AT&T team, which was obviously a large team, and it just felt like a family. After the internship, I went to back to school, finished up my master’s and CPA, and started with EY full-time in both the assurance and M&A practices. That gave me the opportunity to experience both auditing and some financial due diligence within the transaction services group. 
I was at EY for about two years when I found out about an opportunity with Gartner. The grind of public accounting was starting to get to me, and it was a position that was within their sales strategy and operations group, so it was appealing to make a pivot to something different. I took the opportunity about 4 years ago and have loved the transition. I’m currently the Global Sales Strategy and Operations Director.

Let’s start with your decision to leave public after. How did you evaluate the opportunity in addition to leveraging your background for a strategy and operations role? 

It was a quick process once I applied, so I couldn’t evaluate much other than the role at hand. The role I joined would be considered ‘entry’ level from a distance, but they were still expecting professionals with a couple of years of experience. This role required meeting with VPs of the Sales department and becoming a strategic thought partner for them. You get an opportunity to shape how Gartner maximizes the value from its largest annual investment, the sales force.
To be successful in TP&A, there are two big items - professional communication and process improvement skills, both of which public accounting helped me learn.
Within auditing, you engage with senior leaders at your clients almost from Day 1. You're meeting with VPs of Finance, Controllers, Senior Managers etc. With walkthroughs, for example, you very quickly must establish an executive presence, prove your credibility, and earn their respect.  Leading so many of those walkthroughs in a short period of time is a great training ground to hone those executive presence skills. 
The second area was process improvement. My experience doing those walkthroughs and documenting internal controls/processes was super valuable for an operations role. Operations is process management. How are things working? How can we improve the way things work to make them more efficient and effective? You continue to shape that questioning mindset that is invaluable for roles outside of public accounting.

Can you explain more what Gartner does, and how your department/role fits into the overall business model?

Yeah, absolutely. Gartner has been in business for about 40 years, and ultimately what we sell is research and advisory solutions for businesses. Those offerings are now tailored for specific executive roles, so a CEO, CTO, or CFO would all have a different product subscription. Within these subscriptions, you get access to leaders that were previously in that role, and they will sit down and help you with key initiatives that you're working on.
For example, maybe you are the Chief HR officer and you’re having a problem with attrition. You can call up Gartner and immediately set up calls with analysts who are focused solely on HR matters. They would then maybe provide you with the top strategies you can implement to deal with attrition or walk you through current market trends with the top companies in your industry. Most of our business right now comes from very established companies, like Amazon. Those companies are very focused on staying on top of the latest market trends.
My team plays into the whole picture by doing the same thing, but for the internal sales departments. We’re working with each sales team to maximize their efforts across the board as they go out and try to find these businesses that can utilize our service offerings. Salespeople by nature aren’t driven by big data analytics or metrics, so we come in with that data-driven mentality to be a thought partner and drive profitable solutions. We’re basically an internal consulting group.

You’ve been promoted four times in the same number of years. How has your role evolved since you started? 

From day one until now can be summed up as process improvement projects but the scale has changed as my time has evolved. At Gartner, we are hiring large volumes of salespeople on a continual basis, so one of my first tasks was focused around how to establish a process to get everyone setup and onboarded – systems, new hire materials, payroll, etc. - in an efficient manner because it was previously just with one-off emails for every single person. 
For the first couple of years, it was just taking on that next project that got me involved with a higher-level priority item and continuing to develop relationships with our senior leadership. About a year and a half ago, I created an investment model that valued every single sales manager at Gartner and how profitable they are for the business. You could input a given salesperson, and the model shows where's the best marginal value for the marginal investment we're making. I was only able to do that because of my background in accounting and financial statements.  It’s funny how those public accounting experiences will continue to benefit you regardless of where you go. 
Now I consider myself more of a portfolio manager, with the 5,000 salespeople as our assets. I evaluate and figure out the best performers. For example, sales would come to us with an idea, and then I run that logic based on the number of people they want to add and where they want to add them. We either accept or reject the proposal and just help drive profitable decision making.

It sounds like you’ve made a career out of taking the initiative of solving problems and not waiting for someone to tell you how to do it. Any insight to that? 

Your managers and management group are invaluable to creating that environment. You want people that will put you in a position where you're not always comfortable. You're always reaching and expanding your skillset to accomplish the task at hand. It’s an ability to give you new projects that are just outside your comfort zone, to where you can still go hit it out of the park, but it’s not easy enough to where you’re not learning anything.
I've been so fortunate that every manager I've worked under at Gartner has provided me that opportunity in our year-end reviews. It’s been a relationship dynamic where they congratulate me on accomplishing the things I set out to do, but are forward thinking and lay out what they think I should do next. If I fail, great, now we know where my limits are at and what work I need to focus on to improve.
It’s probably the biggest thing that was missing during my time in public accounting. You’re given your roles and responsibilities, but you’re confined to the established promotion track and can feel restrained if you’re outperforming your peers or the current role you’re in.

Is there any routine in a strategy and operations role or is it just attack the issue at hand? 

A lot of it is project-based where we’re just trying to figure out the issues with the sales team and if there are opportunities, how we can solve for those. It’s a job where I am not ever doing the same thing every week.
There is a little routine since I’ve been leading the territory investment strategy. I've changed our corporate strategy towards evaluating decision-making on a rolling quarterly basis, as it used to just be on an annual basis when we set forecasts. In that environment, the CEO would set the number of sales roles we could add for the next year, and then we would disseminate those throughout the organization. I've now reversed that where quarterly, we review our sales performance and figure out what adjustments need to be made to achieve the growth goals for the next 3, 6, or 12 months. It’s helped us readjust our planned allocations and make sure we’re heading in the right direction for both the short and long term.

To close, any forward-looking insight?

I'll say I think in more present terms, I keep my eyes out and ears open for opportunities everywhere. I am a very curious individual that, if a friend calls me and says, ‘I think I have a job for you’, I'm absolutely listening because I don't think that hurts in any way. My actual boss right now encourages people to listen and learn about other opportunities.  You never do that when you're a public accounting because you're too busy working all the time. Something I would have told myself back then if I could, would be to look around at your clients.  What are the different jobs people do? It’s a first-hand insight into what other opportunities are out there. 
Forward-looking, I don’t really have a five- or ten-year plan. The way I look at it is, over the next year, am I going to be put in a position where I can develop certain skills I hope to attain? If that can be accomplished in my current role then great, but if not, I’ll probably look around Gartner first to see if there is a role that matches on what I’m looking for before venturing outside of the company. 
And finally, it’s important to ask yourself whether you have the mentors or leaders you can talk to regarding professional and personal growth. You can either assume the direction you’re heading is the right path for where you want to get to, or you can rely and trust on the trusted mentors to help you make decisions for your future.
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