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On today’s show, Lee Fisher, Vice President for Public Sector at Docusign discusses how public sector selling professionals can bring more value to their customers to help them achieve their mission.
Lee will be a featured panelist at the hybrid IEPS Selling Essentials Workshop “End of Federal Busy Season Selling Strategies” on August 7. Learn more and register here.
Find Lee on LinkedIn.
LEE’S TIP: “You have to be good at a lot of things now. Knowing your missions, being consultative, being a master of your craft, using AI. And successful sales reps really care about their personal brand.”
THE PODCAST BEGINS HERE
Fred Diamond: We’re talking today with Lee Fisher from Docusign. Lee, I’m excited to have you here today. We’re doing today’s interview right before July 4th in 2025. I’m in a big building, there’s three cars in the parking lot, so people are taking their early vacation, but I’m excited to talk to you. I know you have a great history in tech sales and in the B2B, business to government space. Now’s an interesting time for people who are listening. Obviously, a lot of stuff happening in the government, in the government IT world. It’s also the beginning of the end of the federal fiscal year, which ends September 30th. Normally, that would be the big story. Lee Fisher, I’m excited to have you here today. Give us a little bit of an introduction to yourself and tell us your role at Docusign.
Lee Fisher: Thanks for having me, Fred. It’s great to be here. A little bit about me. I live in Northern Virginia. I’ve been in the DC area now about, let’s see, I graduated college in 2003. I went to the University of Virginia. I was an out-of-state guy, and I graduated in ‘03. I’ve been in the area ever since then. I am definitely a family-first guy. I consider myself very blessed there. With the little time that I do have outside of that and work, I like to exercise. I like to read, although most of that happens on airplanes these days for me. I’m trying to pick up golf, I’m not that great at it, but I do have fun playing it.
I’m here at Docusign. I lead our public sector sales business at Docusign. I’ve been here since February, so a few months now, five months. Prior to that, I was at Salesforce for six years. MuleSoft four of those six years at Salesforce. MuleSoft was acquired by Salesforce. Fantastic company, amazing experience there. Prior to that I was at Oracle for over a decade. I was there for quite some time. I know you know plenty of folks that are there that you’ve worked with over the time that you’ve been doing this. I got my start at a company called GTSI, which was a reseller, if you remember that name. That was over 20 years ago now. I’ve been working with the public sector on the provider side, but I’ve been working with the public sector for going on 23 years now.
Fred Diamond: I actually remember GTSI very well. I began my career at Apple Computer and then Compaq Computer. I spent a lot of time in Chantilly working with those teams in the mid-90s, working with GSA schedule and stuff like that. I mentioned it’s an interesting time. We’re doing today’s interview in the beginning of July. What are the biggest issues facing sales organizations that are in the B2G, the business to government space right now?
Lee Fisher: There’s a few things that I would say to that. One is, and this could be B2G, but I think in general this is the case, which is that customers, consumers, buyers, they’re just way more knowledgeable now than ever ahead of a sale. I’m a buyer, you’re a buyer, I buy things as well, and I know what I want. My expectations are super high. I expect personalization. That’s only going to become more and more true. That part of it is challenging.
The market’s more crowded, so competition’s high, and even in public sector, that’s the case. There was a time, I think, when public sector was always a step behind the enterprise markets and that sort of thing. I think what we’re seeing now is the federal government, GSA and others, they’re making a very good effort at this to change that. The way to get in for FedRAMP low is not a lot easier. Now you’re seeing a lot more competitors. That, of course, is on the selling side a challenge. You got to be on your game.
Another issue that I think sales organizations are facing is how to best use tech and data, which is a good problem, but there’s so much of it and it’s moving so fast. Then how does each sales organization get really good at figuring out how to enable the sales organization on those sorts of things? I think that is a challenge. Of course, economic uncertainty. I think we’re all pretty well aware of that one, economic uncertainty, budget scrutiny. How do agencies do a better job at consolidation using what they already own? Those are all things that exist.
Amongst all of this, we haven’t really seen, at least from my purview, I don’t think we’ve really seen the sales cycles shorten, at least not in the government space and not in even the enterprise markets. I think the sales cycles are still longer. You look at the challenges and you go, and my speed to business isn’t necessarily moving any quicker, so the combination of all of those things, I think, makes it harder on a sales organization.
Fred Diamond: Interestingly, you didn’t even bring up AI, which we’re seven minutes into the interview and that’s thrown a whole bunch of different loops. I didn’t realize you were at GTSI, but I’m flashing back to days when I worked at Apple and Compaq and we would do full-day briefings for customers on our five-year technology plan. Now a customer can type into any of the GPTs, what is Apple’s five-year product plan, and they can get that information instantaneously.
You also make a great point there concerning the speed of the sale. It’s always been in the customer’s hands. The customer dictates it. Either it can go really, really fast for some reason, or it will go at the same speed. We do talk about this a lot in the Sales Game Changers Podcast, what can you do to possibly influence that and what you really can’t do? I’m just curious, you deal with a lot of government customers, you’ve been on the B2G side your whole career. What does the government and other public sector customers demand from sales professionals right now? I’m just curious if you can make a distinction between the average customer and maybe public sector leaders. What are you hearing? What are they telling you? What are they demanding from you?
Lee Fisher: It’s a great question. What we see is customers are going to expect, and by the way, I think the expectations are fair. I actually think they are totally fair expectations, but they expect if you’re walking in there as a sales account executive for said accounts or for said agency, that you are going to be a mission expert on that agency, because you can be. Everything is public knowledge, you can study ahead of time and come with a really strong point of view and understand their mission. Having already done your homework, put the time in, is an expectation we see.
Understanding how they buy, understanding who all the stakeholders are in that organization, having a really strong point of view on value. The word value almost gets… My guess is if I’m on the customer side, I might actually start to hate that word, because it gets thrown around a lot, and it can be misused or not taken seriously. But if you’re doing it right, in my opinion, being able to figure out what true, quantifiable, measurable benefits are, and bring those to the table. Are you doing the homework ahead of time? Have you collected information on things like time saved or operational costs, or security vulnerabilities, or mission improvement areas that are quantifiable? You have to be able to come with some of that, and that’s an expectation, and I think a fair one, especially in the government space. Because taxpayer money, we should be treating that like it’s our own bank account because it is.
Fred Diamond: For previous listeners of the Sales Game Changers Podcast, we did a survey of the words that were most uttered on the Sales Game Changers Podcast. Number two was empathy, and number one was value. I talk about this all the time. People ask me, what do customers need? I’m like, they can get the information, the specs and features, and general benefits in a second by typing into the internet. For you to have even some degree of value to the customer, you need to be, I tell people, a step or two ahead. Every public sector customer is mission driven. They’re not looking for profits. Maybe they’re looking for cost savings, of course. There’s no excuse for you as a sales professional not showing up.
I’m just curious, for Docusign specifically, we didn’t really talk too much about exactly what Docusign does and is, and I don’t want to make the presumptions for listeners. How are government customers using your solutions right now?
Lee Fisher: Everyone knows Docusign for e-signature. Everyone knows Docusign for that. You’ve probably used it. I had used it before I came here.
Fred Diamond: Used it today.
Lee Fisher: I’ve used it on my leases and getting a mortgage, whatever it might be. I’d used it before I came to work here too, for sure. This Monday, meaning a few days ago, June 30th, was actually the 25th anniversary of the E-Sign Act, which was a foundational piece of legislation at the time. 25 years ago, that was a very forward-thinking piece of legislation. Docusign is known for that. We pioneered that technology, but we fundamentally changed how people conducted business, helping businesses and governments connect with signers at a time and place that’s convenient for everyone. That was the genesis of that when it came out. Then a whole e-signature industry sprung up around our efforts.
When we pioneered it 20 years plus ago, we were solving a very acute problem, a problem that still persists, by the way, very much so, especially in the government space, but it doesn’t solve all problems for end-to-end business agreement or government agreement management. Now, what we do is, for the government and for others, we go beyond simply streamlining the commit phase of the e-signature component. But that’s just the tip of the iceberg. We’re also driving value now through AI. We’re driving value through what we call the Intelligent Agreement Management platform, which is our AI platform. This is addressing all the risks from start to finish in that agreement process.
Now, don’t get me wrong, while AI is where we’re going, or a lot of companies are going, that original problem statement that sprung up over 20 years ago, which is getting from paper to digital, that is still a massive potential area of efficiency improvement in the government. The federal space alone, 98% of all the forms out there are still paper.
Fred Diamond: Wow. 98%?
Lee Fisher: Yeah. The feds deal with over 10,000 unique forms, which there’s 106 billion pieces of paperwork that are transacted upon annually. When you factor that out, that’s 38 to 39 billion to tax taxpayers in terms of dollars and cents. It’s still a huge market that can be up-leveled today, and that is still a big part of our market. While we’re going towards the AI space, which is getting everything you can usable out of an agreement, because a lot of data is trapped in these static PDFs and forms, and as a company, we’re innovating in that space. But specifically too, just how do we get from paper to digital still? That’s still a big component of this.
Today we’re in every one of the 15 federal executive departments. We’re in all 50 states. We’re in over 5,500 unique customers across both state, local, federal, but also higher education, not-for-profits. We’re FedRAMP authorized, we’re IL4 compliant. We’re in a lot of places and we’re doing some very cool things as we get into the AI space. But even just the simple efficiencies around paper to digital is still a big area for us.
Fred Diamond: What are your top priorities right now? We’re doing today’s interview in the beginning of July of 2025. What are your top priorities as a tech business leader this week? What are you focusing on?
Lee Fisher: I got here four or five months ago, so things I’m focusing on now might have been a little bit different than a year ago when I left, when I was at a place that I had been a leader for several years. We’re focusing on a culture of figuring out that value selling motion because it is an important one, which is making sure you do understand exactly what a customer needs, not just trying to hammer your product home. Adoption’s a big one for us as well. Making sure that everybody is fully using what we sold. That’s a big focus area for us. Operational health and strategy is pretty big for me. Things like data-driven forecasting, inspecting the business every week, pipeline health, you have to be an expert at that now.
The other thing we’re focusing on too is I’m a believer that wherever you work, anyone in the company, it doesn’t matter if you’re in sales or not, anyone in the company should really, really be able to carry the company message. Can you do that elevator? I think any single person in the company should be able to do that and do that well. We’re building the next generation of leaders as well. I believe that every leader owes the right to be a mentor and to find a mentor in your life. It’s one of the things I actually really enjoy about the role.
Then we’re adopting AI. Docusign is very big on that. We do a lot of training here on things like Gemini to get everyone here very comfortable with using it and maximizing the value of that in your daily work life. That’s another big focus for us too. I can tell you, rarely does a day go by for me that I don’t use either Gemini or GPT or something to help. It’s there, it’s a great tool. How we get that everyone’s an expert in that is also a big focus area for us.
Fred Diamond: We also started a sub-brand of the Sales Game Changers Podcast called the AI for Selling Effectiveness Podcast. We post that show every other week. Actually, as people are listening here, you just made a really great point where you said you like to mentor and grow the leaders. At the Institute for Effective Professional Selling, we have our Emerging Sales Leader Program. It’s a month-to-month program. It’s virtual in the middle of the month. We bring on close to 20 sales leaders who are early in their career, but have just made the move to leadership. That’s a program we’re very proud of.
What are the best sales reps doing right now? You talked before about the sales process, how in some ways it still is going as it’s going, but the reality is, a lot of sales reps that are in the middle are getting flushed out, because customers don’t need them if they’re not bringing true industry value. I remember I once spoke to a great sales leader who said to me, “You can either bring great product knowledge or great industry knowledge to your customers, but you got to be above the fray, or else you’re just not going to succeed.” What are the top elite sales leaders and sales professionals doing right now?
Lee Fisher: That’s a great question. What you just referenced that you had spoken about with someone prior, it actually has me thinking a little bit because I can remember a time early in my career when I was an account executive in the field. I remember the people who I emulated, they were really good at something. That person, either they were the relationship person, or they were the person who just researched the heck out of an account and knew it inside and out, or they were the connector, they knew everybody. People were good at different things, and that made them successful. I think that doesn’t get you there anymore. Meaning, you have to be good at many things now. That one thing isn’t good enough. You have to be good at a lot of things now. Knowing your missions, being consultative, being a master of your craft, using AI, we’ve talked about some of those today.
The one I would probably add to that is really successful sales reps, I think, they really care about their personal brand. There’s something about waking up every day and going, “If my CEO right now could see everything I was doing, is it optimal?” I think to me, that’s always been something I’ve seen with folks that operate at a high level. They care about the brand.
Fred Diamond: Let’s talk about that for a second. If you’re managing a sales professional, he or she, they’re 10, 12 years in their career, maybe they’re at a lower-level manager level. What would be some of your advice on how they can grow their personal brand? Are you talking about your brand in the industry, your brand in the company, your brand as someone who works for me? Talk a little more about that.
Lee Fisher: That’s a great point actually. I mean both, both inside your company and outside your company. I actually would argue it even crosses over into your personal life. It does. Who you are, the integrity of who you are as a person, I think it goes across all of those factors. But that aside, some things that I think stand out to me for brand and how people can get really good at that, is when it comes to customers, I think leading with outcomes to customers, not hammering the product. Understand the customer language and how to speak to them. I think that’s an important one. Being super prepared when you go into those customer meetings, which we talked a little bit about. Don’t waste people’s time. You don’t have to.
Everyone knows a lot about Challenger sales, probably most people that are in the sales industry know that. I think that is a component of it as well. Someone who’s not confrontational, but somebody who is able to get you as a customer to think different to challenge and to come with new thoughts and ideas. On the customer side, consultative, challenger, well-researched, those are important components. Then internally as well, I really think the great people have a voice. I will tell you, as a third-line leader, yes, I learned from the people above me. No doubt, they’re fantastic. But honestly, in a given day, I learned more from my team. It’s the folks who really come forward with ideas and thoughts and, “Hey, wouldn’t this help us make our company better if we tried this?” Even being challenger internally is also something I see work very well for folks in their careers.
Fred Diamond: I’m reminded, we have a friend named Lee Salz who wrote a couple books. One is called Sell Different!, one’s called Sales Differentiation. Even more than ever right now is you as the sales professional, and sales leader for that matter, you need to differentiate yourself, and it is by some of those things. Bring in ideas, thinking about where your company’s place is in the industry. What do they say? It’s simple, but it’s not easy. It’s simple to think about that. It’s not easy to implement and execute. But the ones who are differentiating themselves are the ones who are truly doing that.
I’m just curious, what are some of your leading guidelines, some of your principles that if I were to ask your team members, “Describe Lee as a leader. How does he differentiate? How does he lead?” What would be some of the things that they’ve sung to that have led you to this level of success?
Lee Fisher: One is, for the guiding principles, I would say my core values are grit, humility, curiosity, coachability, diversity, and integrity. I wish I had a top five, because that’s six, but those are my six. Those are the six that I probably care the most about and I try to surround my core values around. I don’t always get them all right, but I try my best. That’s what I would say are my values.
Now, as for describing me, I got to say, over the years, I’ve stolen things from other people that I liked in leadership and other capacities. I’ve purposefully not tried to adapt things that I didn’t like. Having worked for a lot of people, and with a lot of people, you see things you like, you try to take them, you think maybe you don’t want to use, and that’s pieced together who I am now. A few of those things, but I’ll just rattle them off to you, really try to empower others around you. Don’t take credit for somebody else’s work. Put people on a pedestal that are doing well, get people raised up, get them promoted, get the good people promoted in your organization. I learned that really early on in the field from J. Smith. He’s been in the industry a long time. I worked for him at Oracle. Great guy, good friend. He was excellent at that.
Try to take care of your team like they’re your family. They are your family. That’s another one for me. Take care of your people. You know Dave Rey probably at Salesforce, his organization, when you look at it, he’s done a fantastic job of that. They’re a family over there. That’s because Dave takes care of his people. That is something I’ve tried to emulate over the years.
Don’t ask anyone in your org to do something you wouldn’t do. That’s another one, the lead from the front aspect. If you’re asking your team to do a stand-and-deliver on the product that just got released this past week, I should be able to do that, not just ask my account executive to do it. Candidly, that’s one of the reasons I came here, because our CEO and CRO, Allan Thygesen and Paula Hansen, if you follow them on LinkedIn, they are on the road every week. They are out there hustling, in front of customers. I’m like, you know what? That’s leading from the front. That’s a good quality.
I’m big on operational soundness. I’ve been very lucky to work for some really excellent people that really know how to just run a business. Like Eric Eyken-Sluyters or John Beauchamp from Salesforce, they’re like machines at that and they taught me how to do it well. Then probably the last thing I’d say is, and this is a simple one, and yet sometimes we’re so busy we forget, is you got to take the time to just say thank you. We run so fast and hard in our jobs, everybody, and that one sometimes can get overlooked, I think just taking the time to recognize and show gratitude to the folks who are doing the right things.
I worked for a leader, he’s now the CEO at Tines, Series B company called Tines, Terry Tripp. I remember, in the year 2000, Terry sent me a handwritten note and it was just a thank you note for something I did at the time, it was an RVP award or something. That stands out to me in my memory, that I got a handwritten note from my CRO who’s managing thousands of people. It’s not like the guy isn’t busy. Things like that too are things that just stand out to me that I have tried to emulate over the years, as best as I can.
Fred Diamond: As you’re mentioning that, I mentioned on the show already that I used to work at Apple Computer, and there was a sales rep who gave me a wooden apple and said, “You’re a good apple.” I worked really hard. I was hustling and all that stuff. I’m well into my career now and I think back on some of those moments. I remember going on a trip with a sales professional guy, I think he might’ve passed on by now, who was probably in his late 60s when I worked at Apple, which was like 30 years ago. I think he might’ve passed on, but I remember he said, “I want to take you for a drive into DC to help you understand what we do.” I was like, “Okay.”
Lee Fisher, it’s great talking to you. You’ve given us so many great ideas here. Give us a final action step, you’ve given us so many great ideas that people can put into play, something specific people should do right now after listening to the show.
Lee Fisher: It’s something I probably mentioned once or twice throughout this podcast today, but I would say if you don’t have a mentor and if you are not a mentor and you’ve been doing this for more than a year, literally anybody can be a mentor, I think, I would say figure that one out. I learned more from that probably than anything, just having some great people in my life that I can bounce things off of who I don’t necessarily report directly to. Although my direct manager, JP Westwood, is fantastic at that as well, but find those folks. I’ve named a few of those people today just in my conversation with you and they have been lasting impressions for me. I think for everyone out there, that would be my suggestion. Find somebody that you can chat with once a quarter or whatever and just talk on those things.
Fred Diamond: Most of those people that you would seek out as mentors would like to be mentors. We talk about mentoring pretty frequently on the Sales Game Changers Podcast. One thing they do say is, “Be specific. Tell me exactly,” as compared to, “How do I improve my career?” Say something like, “How do I go higher in my customer’s organization?” Or, “How do I build stronger relationships at the C-suite?” Or, “How do I balance my family life?” whatever it might be, but they all say the same thing, “I’d love to mentor you, but come specific so that I can talk about experiences and things like that.”
Lee Fisher: I agree. One thing I’ll add to that too is what’s really cool about that that I’ve noticed over the years is actually some of the things I’ve really learned and taken are not necessarily from people that are even higher ranking. Yes, some of my best mentors that I mentioned today, they are higher ranking, they’re further along in their career than me. But I’ve also been a mentor and I’m like, “Man, as the mentor, I’ve learned more from this mentee than I knew before.” Really, there’s so much knowledge out there and great talent and people to talk to. The more you can network out there, I think the better.
Transcribed by Mariana Badillo