Deep Dive

Modern Performance Deep Dive: Bridget Gleason, VP of Worldwide Sales at

Modern Performance Deep Dive: Bridget Gleason, VP of Worldwide Sales at

Bridget Gleason (LinkedIn, Twitter) grew up a witness to the value of swimming against the tide. Along with five sisters and an older brother, she first experienced the concept of calculated risk by watching her father become a serial entrepreneur at a time when funding was hard to come by, and venture capital meant a trip to the bank. After a decidedly traditional start at Xerox, Wang Laboratories, and Hewlett-Packard, Bridget found herself taking a calculated risk of her own. Wanting to control her own schedule and spend more time with her young children, she opted to start her own company. Suddenly she was hiring and managing other people, something she’d never done before. This comfort level with risk and entrepreneurship led her to sales management and ultimately to be the VP of Worldwide Sales at In this interview, we discuss what she’s learned over a noteworthy career, including topics like the importance of internal dialogue, identifying roadblocks using metrics, and empowering team members to solve their own problems.

What are the characteristics you look for when hiring for high performance?

Success leaves tracks. So I look for people, even if they’re right out of school, who have a record that demonstrates motivation and a drive to be excellent.  Whether it’s the captain of the water polo team or someone who worked to get their pilot’s license, they’ve shown themselves to be driven and goal-oriented, and can point to milestones of success in their life.

2016Gleason0731_C5x7Web“I ask job candidates to give me a narration on their career. I listen for the story they tell themselves, their internal dialogue.”

Why do they say they’re applying for this particular job? How do they think they got into a certain school? If their internal dialogue is optimistic—if they think, “I can overcome. I achieve. I overcome obstacles”—then that’s the person I want on my team. That’s where you can often find evidence of resilience, persistence, and tenacity. It’s important that they have a positive outlook and believe that they can overcome obstacles, because in sales you run into a lot of setbacks.

Hear more about hiring high performance Account Executives here:

What kinds of exercises or interview questions do you use to test for high performance during hiring?

I ask candidates to tell their story. I listen carefully and ask questions that may seem emotional in nature. “How did you feel about that?” or “How did that impact you?” I’m listening for that inner dialogue. Then I have them do a mock presentation or discovery call about my product. At we sell a very technical product, so it’s unlikely, unless someone has been in that space, that they’re going to be able to answer technical questions. It puts the candidate in an uncomfortable situation. They’re not going to know all the answers.

“A mock discovery call during the interview process gives me a good glimpse into how they handle themselves when they don’t have all the answers, when they’re uncertain and uncomfortable.”

Do they get nervous and panic, or are they able to rise above it and still connect with the customer?

Hear from other experts on testing Account Executives for high performance here:

What’s the secret to effective staff onboarding?

I always have a formal onboarding and I’m responsible for putting together the agenda. There’s a well-thought-out, structured plan for at least the first two to four weeks to ensure that new hires actively participate. I’ll have new hires find our three biggest competitors, research the primary features of their products and how they differ from ours, and present to the group. Sometimes that requires digging, going online and researching who they are, or signing up for their service. They have to put a lot into it to get a lot out of it.

“From day one, new reps are also working on getting what we call ‘Solutions Certified.’ They learn how to conduct a compelling discovery call, give an effective demo, and pass a written test demonstrating knowledge of the product, the market and our company.”

Not everybody passes the first time. If they don’t, they keep trying within a certain period of time. We might give feedback, like “You didn’t do enough discovery to tease out what the use cases and benefits are. You’re going to have problems running the sale.” Finally, onboarding is not a one-and-done. It needs to be ongoing and reinforced. Every week we do demo practice. At my previous company reps were asked to be what we called ‘audible ready’. At every sales meeting, we’d bring up a topic, and people would have to be ready to talk about a product, feature, or market at any time.

Hear more about Account Executive staff onboarding here:

gleasonHow do you communicate culture when adding new team member?

So much of that starts with who you hire. It’s really important to hire to the culture first. You can communicate all you want, but if you don’t have someone who naturally fits the culture, then there’s often a disconnect. We may have a team culture that’s very collaborative and team-oriented, where we help each other, talk about deals, and share best practices. If I bring someone into the mix who has thrived saying “It’s all about me making my number and my quota,” then I can communicate what the culture is, but it may be a mismatch. Also, the most powerful communication is how we behave as opposed to what we say.

“We can have posters on the wall about our culture being transparent, but if we’re not behaving in that way, the poster is meaningless.”

I look for opportunities to demonstrate, with actions, what our culture is. Once people join the team, it’s also their responsibility to be bearers of the culture. When you have someone new start, rather than saying, “Here’s who we are,” let’s show who we are.

Learn more about communicating Account Executive culture here:


What’s the secret to an effective one-on-one?

I want one-on-ones to be about finding ways that I can help each individual be successful. So it’s important to listen and to be a good listener. I have to be careful not to solve their problems for them.

“There’s a fine line between removing the roadblock and giving team members the tools they need to solve whatever problems they’re encountering.”

For starters, the person who I’m having the one-on-one with owns the agenda. I am at his or her service. Also, being honest and giving honest feedback, both positive and negative, is very important in one-on-ones. We discuss professional development and whether they are getting the experience and support they need to grow. These topics shouldn’t just come up at the end of the year in a annual review.

More from other experts on Account Executive one-on-ones  here:

What’s the secret to an effective team meeting?

I’m not having meetings for my own sake. I want everyone in the room to understand why we’re there, and how we can benefit if we keep on task. One of my pet peeves is laptops and devices in team meetings.

“When people get distracted, meetings go longer. Treat the team meeting like a flight and put your device on airplane mode.”

I’m okay keeping the meetings short, but let’s everybody be present and be in the room. Always have an agenda ahead of time, check in with the team and ask if we’re on track in terms of the agenda. If people aren’t tuned in, then there may be some adjustments that need to be made during the meeting. I also make sure that meetings are participatory. So if we’re doing a forecast review, I may have the manager of that pod lead the meeting. If it’s a product announcement, I may ask a different person; I don’t want it to be just me talking. Typically in a team meeting my goal is to speak less than anybody else in the room.

More experts on Account Executive team meetings weigh in here:

What role do performance metrics play in one-on-ones and team meetings for you?

At a team level, performance metrics give me a clearer picture of what to expect, help me diagnose any problems, and help provide motivation to team members. For instance, if eight out of ten of the reps have a 70% conversion after Proof of Concept (POC) and I’ve got one that’s at 20%, I know there’s an issue there. If everybody’s around 20%, then it shows me there’s a different issue.

IMG_1021“Metrics help me identify where problems and bottlenecks are, where I can help the team improve, and where maybe it’s the product.“

Top sales reps keeps very careful track of their metrics because they want to be able to diagnose themselves. They also want to know what the team’s metrics are, because if somebody else has an 80% conversion from POC to close, and theirs is at 60, that tells them, “Mine can get better. What are they doing that I could be doing?” So I want metrics to be a motivator rather than punitive.

Learn more about performance metrics in one-on-ones and team meetings here:

How do you ensure individuals are communicating well with each other?

“Managers need to model effective communication. The best communication is open, honest, and respectful.”

At my last company all of my managers read a book called Nonviolent Communication to learn how to get difficult points across in a way that is respectful. Also, when reps come to me with an issue I always encourage them to go straight to the source. I’m happy to be there, but let’s try to be open and honest with each other and keep things transparent. Unacceptable behavior needs to be called out. It’s another practice that has to be ongoing, because emotions can flare up quickly. It’s important to be able to go back to teammates and colleagues and ask for a do-over, saying, “You know what? I’m sorry. I had a bad reaction to that. Let me start over.”

Read more from other experts on individual communication here:

How do you ensure you’re communicating well with your staff?

Most of my team is in Tel Aviv, ten hours ahead of me. Most of them speak Hebrew first and English second. So we deal with language differences and time differences, and much of time we’re not working simultaneously. I’ve spent a lot of time in Tel Aviv. Because that face-to-face time really helps in our relationship. So when we’re apart and dealing with difficult issues, there’s already a connection.

“I try to over-communicate. I’ll often say something and also send an email summarizing it.”

Whenever possible, I’ll try to pick up the phone and have a conversation. We use Google Hangouts, so we can meet face-to-face, even across thousands of miles. There’s something about having the visual. A CEO once told me that his motto was, “No good news. No bad news. Just news.” He wanted to maintain an environment where people felt comfortable to come to him with anything. I try to model that, to be non-reactive, so that people feel comfortable and trust that they can share anything with me.

Hear more from experts on Account Executive staff communication here:

What’s the secret to effective delegation?

During one of my early management jobs, the joke went that if you raise your hand with a suggestion, that the task would be delegated to you. So now, often that’s the type of person I will delegate something to. When somebody has an idea and they’re excited about something, they’re often a very good person to take on the project and own it, as opposed to me taking it on. An executive coach once told me that I collect a lot of monkeys. She said, “Whenever someone on your team comes to you with an issue, you take that monkey and you strap it on your back. Pretty soon, you’ve got the people who work for you light as a feather.”

“Effective delegation means you don’t take other people’s monkeys off their backs. Help them solve the problem, but you don’t need to solve it for them.”

If someone comes to me with a roadblock that’s slowing their work, I ask for a list of recommendations, and tell them we’ll review them the next week in our one-on-one. It helps because that person, then, takes ownership of the issue. They feel empowered, and as busy as I usually am, I don’t become the bottleneck.

How do you make sure you’re delegating enough?

When I feel like I’ve got too much on my plate and I can’t get everything done–which is every day, by the way–I have to look at a couple things. Am I prioritizing properly? Am I effective at the things that I need to do? Are there things that I’m doing that someone else can be doing, that I need to delegate? I don’t ever get everything done at the end of the day.

“I’m very careful at the beginning of the day to prioritize. If I see that my schedule is out of whack, then I have to go and apply filters and criteria.”

Are there items that just should fall off because they’re not as important? Are there tasks that I could be doing more effectively? Are there tasks that I need to delegate? So that’s a continual process on a daily and weekly basis.

What’s the secret to setting goals for individuals?

“The key is making sure team members set their own goals, so that they own them.”

LinkedIn Profile portraits, great headshot,Let’s say the company sets their quota at 100k for the month. A team member may tell me that their goal for themselves is 50k. A gap that wide requires a conversation where I help them get to a different goal. It’ll start with questions. “How will that play out for you if you hit that goal, over the month, the quarter, and the year? Is that a goal that you’re going to feel good about if you achieve? Do you think the company will view that as success? ” With these questions, you can uncover what’s behind their goals. Then I tell them that before we can talk about how to get you to 100k, we need to have that as a target. I can’t make you want that as a target. If they feel like it is something that I’ve imposed on them, there’s not a good likelihood of them achieving it.

What’s the secret to setting goals for teams?

Like with individual goals, the more I can bring the team into the process of setting team goals, the more likely it is that they’ll own and achieve them. If it feels like the numbers are coming down from on high, then it’s more likely they’ll resent our goals or view them as unrealistic.

“Rather than dictate goals, you’re trying to move what they believe they can do closer to what the company believes they can do.”

When I talk to the team about what numbers we should commit to, it’s a very similar sort of conversation as it is with individual goals. What do we want, as a team, to be our goal? How do we want the rest of the organization to view us? How do we want to be known?

What strategies or tools do you use for tracking goals?

Salesforce is our system of record. So whenever I can keep data and performance metrics centralized in Salesforce, I do. Sometimes we handle some tracking in Excel, but I try to stick to Salesforce. That way we have one place to look for dashboards and key performance metrics.

What are the most important individual metrics to track for performance?

I work backwards, starting from quota and focusing in on each sales cycle. I’m going to look at what their revenue is, then I’m going to look at how many Proof of Concepts (POCs) they are initiating, because POCs have a really high close ratio.

“I know if somebody does x number of POCs in a quarter, they’re going to hit their number. So I can just look at POCs and say, ‘Yep. That looks pretty good.’”

Then I look at discovery calls: when you’ve actually got somebody engaged. If they do a certain number of discovery calls, I know 80% of those will end up in POCs. This leads back to raw activity. How many phone calls do they need to make to get one discovery call? There are countless metrics you can track. I try to get it down to the smallest number I can, but these are the ones that I tend to return to.

What are the most important team metrics to track for performance?

I try to keep the individual metrics the same as what we look at at the team level. So I look across the team as a whole and see how they’re doing against the same metrics.

Which metrics are the hardest to track?

Certain metrics don’t come with much context. Say a rep has had a phone call. It’s hard for me to track if that was a positive or a negative experience for the customer or prospect. Did it move the deal forward or backwards?

“Just because they may have made a phone call or sent an email and got a response, it doesn’t mean that got us any closer to a deal.”

I can see that they got a response, but it takes the rep to indicate whether that response was positive or negative in the context of the conversation.

What are the qualitative performance things you like to pay attention to that are hard to instrument?

“Some of the soft skills: rapport, emotional IQ, meeting quality, and phone skills are hard to quantify, but also really important to understand.”

It’s hard to quantify rapport or a rep’s emotional IQ. If they tell me, “The prospect loves us. The meeting was so great,” and then we lose the deal, I’m left trying to deconstruct what happened. Some people are better than others at reading situations, and you’ll often see that their overall conversions will be better. But to address emotional IQ you have to sit with them on a lot of phone calls, and in a lot of meetings, to see where their gaps are, and coach them that way.

How do you inspect work to look for opportunities for coaching?

Again, one of the reasons to keep track of performance metrics is because then you can see where the gaps might be. If a rep has a lower conversion rate between demo and POC, I know to go see what’s happening within the demo that they’re not converting. I can start sitting in on demos.

image_uploaded_from_ios_1024-2“Instead of just saying, ‘Hey, you’re not making your number,’ I can look at conversions from stage to stage, identify where the problem exists, and tackle it there.”


I use Salesforce conversion data as a starting point to dig in and provide more feedback and coaching.

What’s the secret to giving effective positive feedback?

Positive feedback is easier because team members are always more receptive to it. Often it’s tied to a high expectation.

“I make sure that I’m not stingy with my praise, but that I only give it when it’s sincere and warranted. When they hear praise from me, they know it means something.”

For example, I have one rep who’s been working really hard, putting in extra hours, shadowing this other, more senior rep. He’s working hard on his own process and technique, and he’s having an amazing month. My expectations were always very high, and it meant something when I said to him today, “Fantastic job. I see the work that you’re doing has really paid off.” I try to tie my praise to something that he or she has done that’s very tangible. It’s not just, “Hey, great job.” It’s, “I saw the work that you did improving your demo skills, and I see now that your conversion rate has really gone up. Great job.” I make it very concrete, so it’s a motivator to do more of that and to continue to work hard.

What’s the secret to giving productive negative feedback?

“It’s helpful if there’s some context already built around the issue before any negative feedback is given.”

Anyone who’s worked with me for any length of time knows that if anybody is in their corner, it’s me. So when I give negative feedback, it is in the spirit of, “I am on your side, 100%, but this particular thing isn’t working.” I had a situation where I fired one of my top performers. I loved this guy, but there were some things that he was doing that were unethical, and I don’t tolerate that at all. When I let him go, he knew. I even said to him, “You don’t have a bigger fan in this company than me, and because I am such a big fan of yours, I need to let you go.” I explained to him I cared about him and will always work to help him, but that he needed this lesson at this point in his career. He wasn’t happy about it, but I think he also knew that authentically, I’m in his corner and I care about him.

How do you do feedback where the answer is measurable (“fewer bugs in the code please”) versus less measurable (“You come off as aggressive, Pete.”)

“Feedback requires examples. One needs to make sure they stick to facts without any sort of judgment or opinion.”

Going with the example provided, it’s easier to say there are x number of bugs in the code. My request is: instead of 50% I want it to be 20%. Be very specific. If it’s less measurable, I wouldn’t say, “You come off as aggressive.” I might say, “I heard this conversation where you said this.” Stick to facts. “Someone said they felt uncomfortable when this was said.” I try to keep it coming from a place of support as opposed to judgment. When people know that you are sincerely rooting for them and want them to succeed, they can take feedback, positive or negative, a lot more easily.

How do you manage professional development in your staff? Why is it important?


Don’t just leave it to an annual review. In every one-on-one I try to discuss professional development. How am I doing, as a manager, in helping you get to where you want professionally?

“I don’t always have positions available at the time when top performers feel ready to move up. So we talk about other things they can be doing to expand their professional horizons.”

Sometimes, I can have them do an informal team lead or help with coaching of new reps. I may ask them to take on a project that’s Salesforce and metrics-oriented, helping track conversions and help team members improve conversion from demo to POC. I may ask them to run the weekly forecasting meetings or have them talk to another team within the company on different skill areas that they’re interested in. I’ve encouraged team members to send papers to conferences where, if the papers were selected, that they would be asked to present.

Learn more from other experts on Account Executive professional development here:

What’s the best way to handle someone whose performance metrics are consistently not up to snuff?

I’m going to sound like a total witch on this one. But I’d fire them. If they’re consistently not performing, we’ve had the conversations, and they’re still not getting it, then they’re not happy.

“It’s better for someone whose numbers are consistently below par to find a situation where they can be successful and are told they’re doing a good job.”

We shouldn’t keep giving ourselves messages that we’re a failure. So I encourage them to find an environment in which they’re able to be successful, because they deserve that. It’s just not good for your self-esteem to stay in a place where you’re consistently subpar.

How do you know when someone is ready for a promotion?

“Someone who’s ready for a  promotion has demonstrated excellence over a period of time.”

They’ve got the respect of their peers. They’ve also probably expressed some interest in moving up, and it’s something that we’ve talked about. I don’t want them to be surprised or feel that I’m off track. Their attitude is positive and they’re a solid team player. Their peers go to them for guidance. When you’re seeing these signs, it’s worthwhile to promote.

More experts weigh in on promotions for Account Executives here:

How do you deal with someone who is highly skilled, but a prima donna?

I don’t believe in prima donnas. They get no special treatment. Sometimes it’s enough to refuse to give them special treatment. They’ll say, “Eh, this isn’t for me,” and find somewhere where someone will treat them as they feel they deserve. Sometimes I have to help them make that decision.

“A prima donna is just not good for the team. If they’re too disruptive, then it’s a similar conversation as it is with somebody who’s a low performer.”

I get a lot of questions, sometimes, from management, like, “What? You’re letting go of the top performer?” But if you’re dealing with a prima donna, then you’ll find that the rest of the team will do much better when they’re no longer in the mix.

How do you deal with someone who was great, but is now a morale problem?

I don’t tolerate morale problems. My first recourse is always to try to understand what’s going on. My team knows I’m in their corner.

“If there’s a morale issue, and the person in question doesn’t feel it can be solved within the context of their current situation, then I want to help them find somewhere where they’re going to feel happy and fulfilled.”

It’s not okay to taint the well with a poor attitude. I tell them that a decision needs to be made. If they can’t be positive, and a positive contributor in the context of this organization, then I want to help them find a place where they can. What I want most of all is to create an environment where they will share with me. Sometimes it’s in the course of a regular one-on-one, I’ll say “Let’s go for a walk and chat.” Former team members remember those walks, remember the positive tone of our conversation, and have thanked me the advice I gave them that helped them get a better hold of their issues.

How do you deal with someone who is very skilled but should be more driven?

It’s hard for me to change somebody’s internal drive or motivation, but there are aspects of the environment that I can change to help them be more driven. Can I be more supportive? Is there something else that’s at the root of it? But how much I can help also depends on how it affects the team. Drive problems are never a good thing, and here’s why:

“When you’ve got A players, they look around and they want to see other A players. If you’ve got someone just phoning it in, A players are going to think, ‘This is not my kind of a team.'”

So I have to watch situations like this very carefully. I don’t want someone’s issue demoralizing other members of the team.

How do you deal with someone ambitious who isn’t quite as great as they think they are?

This happens all the time. It’s very, very common. In fact, I think it’s a human condition that we think we’re better than we are.

“It begins with being able to give honest feedback.”

If they’re really ambitious and they know that my interest is to help them get better, then I can help them identify where their gaps are so that they can achieve and realize the ambitions they have.

How do you deal with a star performer to make sure they don’t get bored or burn out?

Reps build up such energy when they’re successful, that you’re more likely to see them getting bored rather than burning out. There’s so much adrenaline involved in closing deals. That always seems to give star performers a little more fuel. But high performers will get bored. They’ve been really successful, and they wonder where they’re going with their development. They’ve obviously mastered this, what’s next? If I don’t have a place that I can promote them or something else they can do, it’s important to be able to tap into other ways. I develop them professionally.

“Even at a small company with fewer opportunities for promotion you can provide opportunities for growth that are often more valuable in the long run than a change in title.”

On getting burned out, that’s making sure that they calibrate. You have to be careful that they’re not expending extraordinary amounts of energy. We’re going to ebb and flow a bit, so we all need to watch that.

What’s the secret to motivating individuals?

I don’t believe that it’s my job to motivate. Motivation is internal.

“‘Rah, rah, rah,’ might energize somebody for twenty-four hours, but it’s not going to motivate them over the long haul, so I look for motivated people and try to create an environment where they can be successful.”

If I had someone on the SMB team that wanted to move to mid-market, I would pair him or her with a mid-market rep on a few deals. I would give that person five mid-market accounts to go after, and and to try to close and earn the commission on them. So I would pick very specific tasks to help the person focus on what they want to do and their career. I try to give them work that is challenging, where they can improve in areas that they’re interested in.

What’s the best way to deal with a team setback?

“Dealing with team setbacks requires a lot of honesty and transparency. Don’t try to sweep them under the rug.”

This is also where leadership comes in. You’ve got to lead from the front. The attitude and resiliency of leadership serves as a model for the rest of the team. It’s part of sales that we’ve got to expect setbacks and constantly be picking ourselves up. That’s the test of who we are.

What’s the best way to celebrate a team win?


The best way to celebrate a team win is to do so together as a group. Do something fun. It doesn’t have to be a big production, but winning together is a great thing for team unity, and everyone should feel a part of it.

“When my son played Pop Warner football, his coach used to say, ‘Every play; every player.’ He was making it clear that every play contributed to the win. Every player contributed to those plays.”

I feel the same way, so I want to make sure that we all celebrate wins together. Every play; every player. Every sale; every salesperson.

What’s the best way to celebrate an individual win?

I like to celebrate individual wins together as well because individuals thrive on recognition.

“It usually means more to team members to be recognized in front of their peers than anything else I can give them.”

So I want to recognize wins in the group and make sure that we all feel comfortable, even though we’re competitive, with celebrating one another’s victories. It’s good for the culture if we can practice this and establish that level of comfort.

What’s the best way to deal with an individual setback for a member of your staff?

Recently, a relatively new team member had a tragic family situation and was out of the office for several weeks. The team just stepped in. They covered his leads, his accounts, and his opportunities. They made sure nothing fell through the cracks.

“It makes me proud when the team steps in for an individual without hesitation. Whether the setback is personal or professional, you want the team to react in the same way.”

At one company, every Friday, we did “beer o’clock.” Everyone in the company was invited, but the sales team initiated it. Being the end of the week, we would go around the room and share highs and lows. It was a way for us to support one another. Oftentimes there were setbacks. Individuals would say, “I lost this big deal,” or “I’m not having a good month.” It was a way for us to come together and support one another through good and bad.

What’s the best way to discipline an individual?

Privately and with a lot of compassion. I keep it between me and that individual.

“I say this a lot, but if a sales rep knows that you’re really on their side, all of these challenges go more smoothly.”

There are people I’ve had to discipline so much that I’ve fired them. If I can still have a good relationship with them, that means that he or she knows I care about them. It shows we communicated, and I got my primary message across—that I’m in their corner.

How do you handle conflict resolution between individuals on your teams?

“At one company, we held communication training. Having training and practice in these areas is very important if you want to have a high-functioning team.”

There’s another book called Crucial Conversations that covers how to communicate when the stakes are high. It requires speaking openly to one another. Be respectful, but direct, and don’t let issues fester. It can be difficult, but let’s have everybody come in the room and talk about the issue openly. I really encourage that. Clear the air. Be respectful. Be honest. Keep it factual as opposed to layering judgment and emotion on top of it. It’s a skill, and it’s really hard to do.


For more Modern Performance Profiles subscribe to our newsletter and follow us on Twitter.