The Sales Career Path of a VP – Jim McDonough

Most sales reps begin their career path with an ambitious eye toward an eventual future in sales management. But not all sales careers follow a straight trajectory – from a sales rep to a sales manager and, if all goes according to plan, to a VP of Sales. Jim McDonough’s sales career path has taken him just to where he wanted to be. After a career in the trenches and learning from the leaders above him, Jim recently left his position as Director of Sales at Mashery to become the VP of Sales at Attendware.

We recently had the pleasure of speaking with Jim about his sales philosophies, his career in sales, and the lessons he learned to get to where he is today.

(Check out our Sales Career Paths Chart to find out where your sales career may be headed.)


Talk about your career trajectory a little bit. What advice do you have for aspiring sales reps looking to take a similar leap to sales management?

Going into my sales career, I had the goals of eventually getting to a VP of Sales role and I thought about how to get there – starting with sales management and moving up. Some of the best advice I got throughout my career was understanding what my current managers’ pains and challenges are – it’s not always just about hitting the number. As a sales rep, I have control over that on an individual basis, but as a manager, what else can I do to contribute to the overall team goal and morale? Early on, I picked my managers’ brains a lot to figure out what kept them up at night and where I could lend a helping hand. That really helped me move up throughout my sales career, being someone on the team that people could look to for help where maybe the manager’s time is stretched too thin – I enjoyed that player-coach role. Understanding what your current managers are trying to accomplish – aside from just making that number – in managing the team and where you can help alleviate some of that pain can go a long way toward helping you get promoted and with lessons to carry on later.

A lot of times your best sales rep, that A++ player, kills it on a regular basis but can never describe how they do it. They look at sales as an art, not a science. That doesn’t translate to being a successful manager at all. If they’re not able to break down how they hit their number, it doesn’t trickle down to the rest of the team.

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What are some lessons you learned leading sales at a company during the expansion-stage juncture of their growth?

The most important thing I learned over the past couple of years during this time is that it’s really easy to lose focus and chase the shiny object, instead of staying focused on what you’re good at and the customers that are already successful with your software. To me, it’s all about honing in on those target verticals and making sure that your lead generation efforts stick around those target verticals – those are the people most likely to buy. We accumulated some customers and figured out where we should be focusing. When we were really hyper-focused on those was when we had the most success. When we veered off a little bit was when you would see a little bit of a dip in productivity and pipeline.

Moving forward, the priority for me is really keeping focus on those target verticals and the different buyers between those target verticals that your messaging is going to resonate the most with. This will keep feeding the pipeline. If you keep chasing that next shiny object, you run the risk of losing that focus and not building a strong pipeline. At the same time, you have to keep an eye on emerging trends.

What is a typical sales process that you like? What are your favorite sales methodologies?

From a process standpoint, I think it really boils down to getting in there and understanding your current customers – how they bought, what was their evaluation process, what were the pains and challenges they were trying to solve – and then really building a sales process around that. If I took a cookie-cutter approach and tried to pop what I did at Mashery into what I’m doing at AttendWare, it’s not going to work at all. Sales process isn’t a one-size-fits-all type of thing. There are certain things I took with me, but the process itself should be dictated by your customers, your buyer and how they like to buy your software or product. If you can align with that, then you can be successful.

In terms of methodologies, I’ve been with three software companies now, and every single one of them has adopted and trained us on the Sandler Sales Methodology. It has served me well over the years, but I recently read The Challenger Sale and have decided this is the best methodology to use moving forward. In my opinion it aligns with the idea of building a sales process according to the buyer’s journey much better than any other methodology out there. I love the concept of Teach, Tailor, and Take Over. It has transformed the way I sell.

In terms of hitting and growing your number, or making drastic moves when you’re off the pace, what kind of activity levers do you think about pulling and what informs your decision?

That’s a tricky one. The activities you’re doing today are going to be the results of closed business tomorrow, depending on your sales cycle. If we’re at the end of the quarter, and we’re trying to make a number, you don’t want to lose sight of your activity metrics – whether its 50 calls a day, or 100 or whatever. I don’t think it makes sense to crank that dial up to 200 dials per day to hit your number – that’s just not realistic. You have to look at what’s in your pipeline – what’s most likely to close now, and focus your energy on those deals in your pipeline that have the most likely chance to close. If you’re fighting that battle at the end of the quarter, unless you’re in a very transactional sale, it’s not going to come from just cranking the engine on activities. Hone in on your pipeline and figure out what you can do to get whatever is in your pipeline and move those forward.

I’ve been in that position as a sales rep, where the manager just panics and forces you to get in 100s of dials and you get so overwhelmed that you lose focus. Maybe you sneak in a deal, but you’re looking at the next quarter and you’re actually hurting your number going forward, if you panic at the end of quarters, instead of bringing in quality pipeline.

What are the most critical keys to managing a sales team?

When I originally moved into management, it was really all about managing people and keeping them motivated and coaching – which is all important, don’t get me wrong – but I didn’t use sales metrics and the numbers to drive my business. Now, everything comes from the numbers. It’s the only way to learn how your sales team is performing so, for me, it really starts with the data, and understanding it and coaching and motivating from that. That’s a really important part of being successful, especially as you scale out a team. You may not have as much one-on-one interaction as you would like, so you really have to understand those numbers across the board.

Which types of sales metrics are most important to you?

It really starts with goals, overall goals, individual goals, team goals and how everyone is performing against those goals. Then you look at how you get there – what activities you need, how many activities you need to create one opportunity, how many opportunities do you need, how much do I need in my pipeline in order to make this goal. Start with the overarching goal and then break it down and understanding the sales metrics over time – how many phone calls to get a conversation, how many conversations to get an opportunity, what’s the win rate on those opportunities. Those are the important sales metrics.

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How important is sales coaching and how can sales managers be better at it? What are the keys to effective sales coaching?

I’ve played sports my whole life, so coaching is critically important to me. Early on in my career, when I first stepped into sales management, it was all about the “rah-rah” stuff. We didn’t have a well thought-out plan based on numbers to get to our goal. I would be involved with the team, hop on calls with them, do role-play, but if you’re not looking at the numbers and putting a roadmap for success for your reps to show them how to get there, I think sales coaching becomes really difficult.

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Once you build that roadmap, it’s meeting on a regular basis – whatever that cadence might be – to make sure that we’re progressing and reaching those numbers. If you take a look and see that a rep is making a ton of dials but not converting any to opportunities, you have to figure out why? Maybe you should focus on the messaging and encourage them to keep up that effort, but be sure that they’re asking the right questions. Every rep is different so to have a one-size-fits all for sales coaching doesn’t really work, and I think I fell into that trap. I kept people motivated, but I don’t think I did a good job of showing people how to get there with the numbers.

More about Jim McDonough

Jim recently started a new position as the VP of Sales at Attendware, leaving a Director of Sales position at Mashery. He also previously worked in several sales positions at SmartBear Software and Acronis, and has a wealth of experience in SaaS sales and sales management. He is an alumnus of the University of Massachusetts, where he was captain of the baseball team. 

Connect with Jim on LinkedIn or Twitter

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