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Today’s show featured an interview with Thom Wright, Regional Vice President of Sales at UiPath.
Find Thom on LinkedIn.
THOM’S TIP: “People leaders are ones trying to find strengths, areas of opportunity and growth for their people.”
THE PODCAST BEGINS HERE
Fred Diamond: Thom Wright, I’m excited to have you on today’s show because some of the things that we’re going to be talking about fit in perfectly, specifically with our Emerging Leaders Program. That’s for sales managers who are either first-time in sales management or they’re on the sales management path. They come from great companies like Amazon, Oracle, Hilton, Salesforce, Carahsoft, Cvent, whatever it might be. I know we’re going to be talking about how you are preparing young leaders for those kinds of roles and get your insights on that as well.
Before I get into my questions, give us a brief introduction. Tell us who you are and I’m excited for this conversation.
Thom Wright: I’m Thom Wright, based out of Lexington, Kentucky. It’s the land of fried chicken, bourbon, and horse racing. A little bit of UK college basketball as well. I’ve spent 30 years in enterprise software sales and over a decade leading sales teams. I actually started at Salesforce, where I spent 12 of my years and got into leadership. I’m now a VP of sales here at UiPath, which is a RPA automation and agentic AI company. I lead a team today as a frontline sales leader focused just on our Fortune 500 accounts and net new logo acquisition.
I’ve built sales teams from scratch more than once. I’ve been to President’s Club and Chairman’s Club 12-15 different times. Also too, I just love sales leadership. In fact, on the side, I run a side business called Impact Beyond Action, where I actually help coach frontline sales leaders. I do that on the nights and weekends. I just love it so much. I love helping the younger sellers too. I’m also ICS certified and trained through the University of Kansas and active practitioner, just not talking about it, but doing it on a day-to-day and I love what I do. It’s a great opportunity to be on the podcast here today.
Fred Diamond: You’re from a beautiful part of the country that I have been to numerous times and I look forward to going back. It’s interesting. We believe, at the Institute for Effective Professional Selling, that the hardest job in almost any company is first-time sales manager. Usually, you’re promoted, you’ve done very well, maybe as an SDR, maybe as an account exec or something, and the company sees how well you’ve done. In most cases, the natural course seems to be sales management moving into a leadership role, but it’s not necessarily the case.
A lot of successful ICs, individual contributors, assume that management is the natural step. I’m interested in your thoughts here. How do you know when you’re truly ready to become a sales manager to make that leap? We estimate it’s 1 out of 20. 1 out of 20 people in early-stage sales will be invited. Just because you want to be in sales management doesn’t necessarily mean that your company or a company is going to put you in there. It’s one of the hardest jobs in the company. It’s one of the most important jobs in any company as well.
Give us some of your insights on if it’s the right move for you, or maybe one staying as an IC, individual contributor, may be the better move for you.
Thom Wright: Fred, the way I think about it is going into management isn’t a promotion. It’s a career change. Those are two different things. I think a lot of top sellers chase the title for money and status, and that is the completely wrong reason. What I would say, I think when I talk to individual contributors that are truly ready to get into sales management, is there’s a couple little litmus tests I think that you can do.
Number one is are you already doing some of that manager work for free today? Here’s what I mean by that. Do your peers come to you for help asking suggestions on stuff? Do you get more out of celebrating a teammate’s win than your own? Those are things when you have what I call that heart change. It’s now about others instead about yourself.
Now, I’ve stayed a frontline sales leader for 10 years, which is crazy. Why? I love it. I love the impact that I can have on the men and women on my team, help them get promoted and move on. But also too, I think like I said, it’s a career change, not a promotion. People do think the only way up is getting promoted in leadership. I also like to talk about when you do get into being a manager now, not all of your time is going to be spent selling. It’s now only about twenty to twenty five percent of your time is spent selling. The other times is around operations, internal stuff, people management, that particular area. I would say follow those three key things when it’s ready to really be that manager.
Then I would also say too, Fred, the other thing that I have noticed, in fact, I was actually just talking to someone on Monday about this, is there are also two types of leaders. There’s a sales leader and a people leader. What I mean by that is a sales leader is great at sales. They get involved in the big deals. A lot of times they win the accolades and the awards at a sales kickoff, top manager of the year, top manager of the quarter, because they are a true sales leader. They focus on the big deals. They either micromanage and get involved or work with their team and they close it, but that is it.
Then there’s people leaders. People leaders are ones that truly care about their team. They’re hiring and promoting the right people on their team. They’re trying to find strengths, areas of opportunity and growth for those people. They’re working to help make those people better, and they know it might only be a year or two years, but that person is going to move on, get promoted, get better. Your AEs know that. They know if you truly care about them or if you just care about the number.
People who might work for a true sales leader may not feel they’re getting growth, they’re getting recognized, or getting help. People who work for a people leader may feel really good about their growth. They feel seen, but maybe that person isn’t truly helping from a sales perspective. You need to be able to blend both working there. That’s what I’ve seen, Fred, but also some things to think about too.
Fred Diamond: The great sales leaders are able to have both. But I like the way you said it, it’s a career change. All of a sudden, let’s say you really enjoyed the sales side. You enjoyed working with customers, developing deals, whatever it might be. Well, now your job is managing seven to eight people. It’s not just managing them, but understanding why they’re not performing, or understanding how they need to be managed, and understanding your management cycle, especially when you’re brand new into the sales management role. Let’s just talk a little bit about that.
Let’s say I was just promoted and it’s a great day because I knew that promotion was something I was striving for. In a lot of cases, it’s not an out-of-the-blue thing where the company taps you on the shoulder and says, “Hey, by the way, we want to promote you today.” You probably know what the path is. You probably know what’s expected. We’ve spoken with a lot of companies where there’s a clear path. There’s a couple of milestones that need to be hit. Then you need to show that you’re truly capable.
Let’s say that you’ve made that transition. You were just promoted, you’re happy, etc., and now you’re given a team of eight. What are some of the things that people might want to do in the first month or two to establish trust as this new being. Now all of a sudden people that I was friendly with, especially if you’re young, maybe I socialized with, went out on Saturday nights because they’re trying to build the team, now you’re in charge. Now there’s a different level of relationship. What are some of your bits of advice to develop that trust?
Thom Wright: Before I answer your question, Fred, you actually brought up something really interesting that I hope people picked up on. If not, I want to uncover it real quick. You mentioned that you just don’t wake up one morning and the company just lays it upon you that now you’re a sales leader. One of the things, if you are looking to get into sales leadership, the worst time to raise your hand for that is once there’s already been a job posting on, say, the internal company job board. That’s a formality. Or you’re raising your hand to your boss a couple months before the end of the fiscal year, “Hey, I’m thinking about getting into leadership.” You’re way too late.
Typically, fiscal year planning starts at least six months before the next fiscal calendar year. You’ve really got to start from at the beginning or early to the beginning of the year to start putting a campaign together, making sure that your boss is aware of your intentions, they agree that you would be a good fit, and get their coaching and help every time you have a one-on-one or who are the people, just not vertically, but horizontally, I need to align to in the organization to have those conversations to get people known.
It’s almost like a political campaign. You’re shaking hands, kissing babies, and building up all that for the moment. Then to the external party, it just looks like, “Well, I guess they just gave them the leadership job.” No, that person has been working for 9 or 12 months on promoting themselves, knowing the right people, getting ready for that role. I really wanted to surface that because I think that’s really important. If you’ve never done that before, that’s why I think working with an organization like yourself, a professional coach, can help you get ready and preface you for what is about to come, to even get into that type of position.
I would say then once you’re in the position, especially if you’ve managed your peers, my first job as a sales leader 10 years ago, Fred, I was in the exact same position of what you just mentioned. These people were my peers. They were buddies and now I’m their boss. What I could recommend is have that awkward conversation in week one. Say out loud to that person the relationship has changed, and I would ask each person on the team how they want to be led. Having that question then almost starts to give you a little roadmap of the best way that person likes to be led and managed.
I’ve made the mistake when I was managing people that I got frustrated because all the other people in my first job at Salesforce as a leader, I wanted everyone to be like me, think like me, operate like me, run deals like me, because I thought, “Well, hey, I went to Chairman’s and President’s Clubs. This is the bar and you have to be here.” Little did I know, until I got into Ken Blanchard and Situational Leadership three years later that you can have different personalities and different people, and the best leaders have a very diverse team. You now just learn how to manage them separately. Number one, have that awkward conversation in week one. Relationships change. How do you want to be led?
Number two, I would also say in your first 60 days, stay in the fight, making sure that you never forget what it’s like to be a salesperson. I think we’ve all seen leaders that as they move up in the ranks, they forgot what it’s like to make cold calls, to do the gritty, dirty work of what a salesperson has to do. Never forget what it’s like to be a salesperson. For example, on my sales team, every week we do what’s called a prospecting power hour on Thursdays. Now, that’s not the only time my team does prospecting, but it’s the one time our virtual team actually gets together, and I’m on that call with them doing prospecting as well. I might be targeting a couple of key accounts, executives. I’m doing the exact same things. I’m dialing with them. That builds so much credibility, but it keeps me sharp of being a salesperson.
Then the third thing I’ll say, Fred, is fix any small stuff fast. Is there something that really annoys someone that you can actually possibly do a quick change for? Maybe it’s canceling a meeting that doesn’t serve the team. Maybe a prior manager had a two-hour forecast call that has absolutely no value or can be put into a 30-minute meeting. That’s a small thing that you can impact and it immediately just ripple change effects across the team to like, “Wow, this new manager gets it. They lead it. It’s really good.”
Then the last tip is to use your resources. Most sales leaders have some kind of CRM today. I hate it so much when a sales manager calls a rep on the phone, “Hey, where are we on this deal?” You know the rep is thinking, “Boss, I just updated my next steps two days ago. Why are you asking me?” The CRM now just becomes this duplicative system for updates. I’ve told my team, “Hey, before I call you to ask for a deal update, I’m going to check Salesforce first. Typically, that’s what I need. If those next steps aren’t up-to-date or there’s nothing in there, then I’ll give you a call.” The rep knows that if I’m calling them, they’re like, “Darn it. I forgot to update my next step.”
A couple of times I’ve made the mistake, “Hey, Jody, where are we on this deal?”
“Well, I did just update it.”
“I’m so sorry. Let me check Salesforce first. I’ll call you back if I have any more questions.”
Having those little quick wins or those quick things makes you come across as a lot easier to work with. You’re still one of them, but you’re also acknowledging there’s a different dynamic. I think that’s a great way to do it.
Fred Diamond: As a hiring manager who’s hired many selling professionals onto your team at multiple places, I’m just curious, what might be some of your, for lack of a better word, pros and cons, some things that you’ve seen during your interview process as you’re trying to bring on someone onto your team that they’ll do that may be a red flag, or maybe something that says to you, “This ain’t the right person for my team.” Conversely, what might be some things that they do demonstrate to you that may get you to say, “I got to have this person on my team. Let’s get them on board.”
Thom Wright: Let’s start with the positive first, the thing that makes me say in my manager mind, “I have to have this person.” Take it down to one word, Fred, they’re specific. Specificity, when they can walk me through a real deal, all the details beginning to end, what went wrong, what changed, those specific details are good, because my test is salespeople are naturally good at interviewing. They’re salespeople. That’s their job. They should be good at that. But I typically like to dig two or three levels deep on a particular deal. “Hey, that’s really interesting the buyer did that. Tell me a little bit more. Hey, how did you do that?” You quickly start to get away from rehearsed answers into what really happened once you’re typically on that second and third level of questioning. The more specific they are, I love the STAR methodology, situation, task, action, result, if they can be specific in their answers, it really makes me know that they know what they’re talking about and they just don’t make it up.
I’ll also say to their questions, what annoys me but also impresses me too, is the type of questions a candidate asks. You know a hiring manager is going to say at the end, “Hey, do you have any questions?” Instead of generic questions, I like if they tell that they’ve done some research and homework either on the role or the company. The questions they ask almost sound like they’re kind of like, “I don’t know if this is the right role. Help me understand,” or, “This is a concern,” where they don’t automatically come across as desperate. I really like seeing that, when we come through, “I really need this person.”
Then also too, I’ve looked also on paper, and when I look at a candidate initially on paper or resume, I could see someone in the resume like, “This person is a killer.” On paper they look great, they look really good. But I find ways during the interview process to provide feedback and coaching, whether that’s someone on my interviewing team, myself, because I want to see how they respond. When I push back, do they engage or do they defend? When I tell them about how they went through something, how are they receiving that feedback? Then applying that during the interview process, because coachability to me weighs heavier than having a killer on paper, because that killer on paper could do more harm than good to the team. Those are the three things for me that just makes me say, “I really need this person on the team.”
Fred Diamond: I want to talk about another challenge that selling professionals go through. I just need to note that we’re doing today’s interview in October of 2026. Thom, I want to get some of your insights on pursuing new accounts. You mentioned before a big part of your successful career has been getting new logos, getting new accounts for your company. That’s a historic challenge. You’re hired, maybe you’re sent into a new territory. We’re also in a very interesting time where there’s been a lot of downsizing and layoffs. If you’re still with the company, the company may say, “All right, here’s 10 new accounts that you need to grow for us.”
Let’s say that there’s no existing relationship, no incumbent business, no obvious reason for the company, even though you have the obvious reason for the company to do business with you, the company may not realize this. Let’s talk about some of your strategies for breaking into accounts. Actually, to be honest with you, that’s something that we do all day long at the Institute for Effective Professional Selling. We know the value that we can bring to B2B and B2G, business to government, enterprise selling organizations with dozens, if not hundreds, in some cases, thousands of salespeople, we need to constantly be showing the value. Give us some of your thoughts and insights for the selling professionals listening on how to start to take this challenge on.
Thom Wright: What I’ll also challenge, for any of these sellers who might start tuning out now in the podcast of, “Well, I’m not a new logo hunter. Let me fast forward. This isn’t relevant.” I’ll challenge you, even if you’re selling into existing accounts, there are business units and groups within the company that don’t do business with your company yet. You still are a new logo seller in a way, even if you’re working on existing accounts. This advice and how we’re doing, I think it’s just as relevant to you compared to if we’re trying to break into Procter & Gamble that doesn’t do any business to the day, just as relevant there.
A couple of things, Fred. Number one, stop trying to get a meeting to talk about you. Depending on what kind of technology or software you sell in the background, you probably have multiple competitors. A lot of people are trying to sell the meeting about us, my company and our product. That is a wrong way to get it. Because these prospects probably get hundreds of emails, they’re quickly going to ignore it. You want to earn that meeting all about relevance, something specific about their business or something specific maybe about a peer company or a competitor that makes that executive read in saying, “Huh, I should actually know a little bit more about this.”
The other thing too is working multiple threads rather than betting on one executive. We have a fun acronym we use here on my team called HOPS, that stands for having other people sell. Instead of just the AE going after a particular account, our AE is having some of our sales engineering team. We have co-primes and overlays. Myself, some of our executive teams, some of our product team members, we’re actually now building out an org chart map and different people have different roles to go after. We’re spreading our bets, multiple threads rather than just one executive.
Then what we do then is we go in where the problem actually lives. Instead of going in with our company or our product, is a lot of the companies that we’re researching are public. They are documenting, billboarding out what they’re doing with the 10K. A document that not a lot of sellers know about for the public company is called the DEF 14A. That is a document that says how every named executive officer at that company is compensated and paid. If you can align where the problem lives with the 10K compared to the DEF 14A and how that executive is compensated, and put that messaging together, you now earn a path right up to someone who sees value and really wants to be able to make that happen. It’s a great way to be able to do it and be able to approach a particular account.
Fred Diamond: As I come down to the end here with our interview with Thom Wright, Thom, just give us three things, three bits of advice. Fifty percent of the audience are B2B or B2G selling professionals, typically SDR, AE, maybe first-line manager, twenty, twenty five percent of the audience is sales leader. Give maybe your three, 10 poll ideas that if you’re on an elevator and you had a minute to give three of your inherent Thomisms, if you will, give us those three things.
Thom Wright: That’s really good. Number one is I would say that it is all about managing up. Most sellers, especially if you’re going to be wanting to get into management, or let’s say you’re running key strategic deals, they don’t know that managing up means you need to learn how to manage your boss and your boss’s boss. Well, how do they communicate? What do they like? What they don’t like as far as updates, and learning about that. That makes your job so much easier and removes so many obstacles. Even if you don’t get along with your boss, learning how your boss operates, what they care about, it almost goes back to what we talked about for Fortune 500 selling, that DEF 14A, how they’re compensated, what the executive cares about. Managing up is, what does your boss care about, and find ways to align with that? That is something that’s not talked about a lot, Fred, but learning how to manage up. There are some great books out there that you can go check on Amazon and be able to do that piece.
Number two, I’ll say that if you’re an individual contributor and you’re bouncing back and forth between, should I be a manager, should I not be a manager. I’m a big fan of Mike Weinberg, and Mike has written a book called The First-Time Manager: Sales. It’s a great, well written book. I know you’ve had Mike on the podcast before as well too, great guy. I would recommend just picking up that book and reading through it. It is a great way to get a sneak peek preview on if this is a game you even want to get into from someone who’s been there, done that, coached thousands of other sales leaders. That would be a key piece as well.
Then number three, I would also say if you’re interviewing, whether you’re maybe actively looking for a role right now, let’s say you’ve maybe gotten laid off and you’re looking for work, make sure that next role you find, it’s hard, especially if it’s been a couple months and desperation starts to come in, you got to pay the bills, maybe you take a job that you’re really not sure about, make sure that you’re also interviewing that manager and that manager isn’t just interviewing you. What I mean by that is understand them. “Hey, what makes you tick? What are your frustrations? What are your obstacles?” Find ways to backchannel that manager, does someone know who that person is, are they good or bad? Because guess what? That manager is backchanneling you and they’re doing the exact same things, because you could add the best on-target earnings and the sweetest product to sell in the world, but if you’ve got a boss from hell, your life is going to be miserable. Making sure that when you’re asking those interview questions, that you’re also interviewing your soon-to-be manager, and being really critical about that too and just not interviewing for the job specifically.
Fred Diamond: We actually interviewed Mike when The First-Time Manager: Sales was published. It continues to be a heavily-downloaded show for us. Thom Wright, thank you very much for sharing your insights. Once again, if you’ve made it this far, check out our Emerging Leaders Program. It’s a six-session program. It’s 100% virtual. It’s held every other Wednesday, typically during lunch, 11:30 to 1:00 o’clock Eastern Time. It’s a great program for sales managers in the first or second stage of their sales career. Thom, a lot of what you hit on is perfect. It’s talked about frequently at the Institute for Effective Professional Selling. Once again, thank you so much for sharing your wisdom today on the sales game changers podcast. My name is Fred Diamond.
Transcribed by Mariana Badillo