EPISODE 652: Get Things Done and Make an Impact with Hacking Your Bureaucracy Author Nick Sinai

The Sales Game Changers Podcast was recognized by YesWare as the top sales podcast. Read the announcement here.

Subscribe to the Podcast now on Apple Podcasts!

Become a partner of the elite Institute for Excellence in Sales (IES) and take your sales team to the next level!

Read more about the Institute for Excellence in Sales Premier Women in Sales Employer (PWISE) designation and program here.

Purchase Fred Diamond’s best-sellers Love, Hope, Lyme: What Family Members, Partners, and Friends Who Love a Chronic Lyme Survivor Need to Know and Insights for Sales Game Changers now!

Today’s show featured an interview with Nick Sinai, He’s a venture capitalist, adjunct faculty at the Harvard Kennedy School, author, former senior official in the Obama administration. He’s the coauthor of Hack Your Bureaucracy: Get Things Done No Matter Your Role On Any Team.

Find Nick on LinkedIn.

NICK’S ADVICE:  “Help your customer be a hero, because it will help you and your company in the long run.”


Fred Diamond: I’m very excited today. We got a really interesting show. We’re going to be talking to Nick Sinai. He’s a venture capitalist, adjunct faculty at the Harvard Kennedy School, author, former senior official in the Obama administration, and he’s had a stint as the Deputy Chief Technology Officer of the United States. Presently, he’s a venture partner at Insight Venture Partners. Nick, I said I was going to have you do your own introduction. Why don’t you embellish that a little bit? Tell us who you are and the reason we’re going to be talking to you today. You came out with your book, Hack Your Bureaucracy, with Marina Nitze. I saw you speak, it was a great book, and we’re going to be talking specifically about some of the lessons that you are sharing for sales professionals, specifically in the public sector markets, the federal marketplace. Embellish that introduction a little bit. Tell us a little bit more about you that we need to know.

Nick Sinai: Fred, I’m really excited to be on this podcast and spend some time with your listeners. I’ve been with Insight Partners almost a decade. I’m a senior advisor there. I’ve been working with Insight portfolio companies, companies that we’ve invested in, to enter and grow in the federal and public sector. That’s been great fun and I’ve worked with many dozen VPs of federal CROs, VPs of government affairs. I’ve really had an up-close view of what works and what doesn’t in selling and marketing in the public sector.

I had the great honor of serving the Obama administration for almost six years, initially at the FCC, and then four years in the White House Office of Science and Technology Policy, including two years as the US Deputy CTO. Then I had a venture capital and management consulting career before that. I have managed to also be a fellow and teach part-time at the Harvard Kennedy School. I live up in the Boston area, and so that’s been great fun to give back and help shape the next generation.

Fred Diamond: Again, I’m based in Northern Virginia, right outside of DC. The Institute for Excellence in Sales that I run, our mission is to help sales leaders and employers attract, retain, develop, and elevate top tier sales talent. I saw you at an event that was hosted by Carahsoft. Carahsoft is one of our strategic partners. It wasn’t too long ago. It was the end of 2023, and you were talking about the book, and then you’re also interjecting some great examples on the selling side. In your book, you talk about 56 different tactics that individuals can employ to better equip themselves for, as you say, hacking your own bureaucracy.

One of the chapters that you had was called Sell, Baby, Sell. As I was listening to you give your presentation to probably an audience of close to 300 companies that sell into the federal marketplace, I was perked up the entire time that you spoke, but I actually got even more perked up at that particular point, purchased the book, read the book, it’s really well written. It’s a fun, informative book that people can read a couple of times and they could also bring to their team as well. We want to focus on some of the lessons about the whole selling side and get your insights. You’ve been a customer, you obviously now are working for the VC world. You’re helping companies get successful into how they could be very profitable selling into the public sector marketplace. Why’d you write the book, and be specific on who it’s intended for?

Nick Sinai: Just as context, Marina Nitze was the 28-year-old SES CTO of the VA. She was told to go fix the VA but wasn’t given any people or budget. Some of the stories we have in the book are her experience, some are my experiences, and a lot more are from our friends and colleagues and people we’ve met in the past decade. There’s just a few fundamental observations. One is that it’s a long game, that it takes sometimes years to make change in organizations, that the hotshot people who come from hotshot organizations, or the outsider often fails coming into an organization if you can see the antibodies. There’s a bunch of maybe obvious tactics, but things that really help people be successful in making change, both at a small level and at a really big level inside an organization. This could be a government agency, but it also could be a large corporation, or your local PTA or homeowners’ association, or nonprofit, really.

We just wanted to capture some of the things that worked and some of the things that didn’t. We had a bunch of stories we wanted to tell. It wasn’t that complicated, we just wanted to find a way to share these. I mentor a lot of early-career technologists and graduate students at Harvard Kennedy School, and I’ve been telling some of these stories and I wanted to put them down on paper.

Fred Diamond: Actually, a lot of the ideas that came through in the book, where I’m not going to say, gee, common sense, because common sense is really hard. Secondly, it’s all about execution. I like the way that as you’re going through the book, you could identify with a lot of things. It’s like, “I could see where that would open up the doors.” You talked about simple things like ordering paperclips, simple things that aren’t monstrous yearlong chores. They’re just simple improvements along the way that can really make the difference.

I’m curious, when you decided to write the book, is the final book what you expected? Or along the path, did you discover new things working with your co-author that you came up with that when you finally published, was it exactly what you expected on day one, or did you come to a different conclusion?

Nick Sinai: No. We initially had in our book proposal something like 8 or 12 chapters. As we were going through the editing process and talking with our development editor, he had made the suggestion that we actually split it into a lot more micro chapters that is specific tactics and smaller stories. I think that helped in the writing and made it more fun. It helps because sometimes you may just think about one particular thing, and we have an appendix in the back, so it’s designed as a reference book, so you don’t need to read it cover to cover. You can actually flip through and say, “This is a tactic that might be particularly helpful,” if you’re stuck. Marina and I use it ourselves when we’re stuck in our organizations or when we’re trying to consult to somebody.

Just as context for the listeners, the first part of the book is about really understanding the problem. How do you get out of the office or the classroom and really understand the problem from the end user? You then also have to understand your organization. 200 people come in trying to make big change in organizations without actually understanding the rules, the processes, and most importantly, the people. Then how do you convince other people that your idea or solution is a good one? There’s a lot of selling, and we’ll focus, I’m sure, a lot of the conversation on that. But how do you sell the idea and how do you show that idea? Then how do you scale it? How do you get more people on the team informally and informally? Then how do you systematize? How do you institutionalize this big change?

We think of bureaucracy hackers as change agents, but it’s not going around the system. It’s actually going through the system, and where you find broken processes and salespeople encounter lots of broken processes, especially selling to government, it is to document them, to help other people understand why they’re broken, and then think about better modernized, fewer processes going forward. But rather than trying to get a waiver and exception or going around the rules, breaking the rules, it is how do you actually navigate the system and how do you do this with people? Because getting stuff done in organizations and certainly making change at scale is fundamentally a team sport.

Fred Diamond: Actually, a lot of the companies that work with us at the Institute for Excellence in Sales, they’re in complex sales, enterprise sales. There are multiple customers, it’s not a one phone call type thing. Sometimes it might take years in some cases for certain business to happen, not just in public sector, but in other large enterprises as well. As I was reading the book, the expression, “It’s simple, but not easy,” came to my mind a couple of times. You still got to do the right stuff. You got to understand the process. People who are successful selling into the public sector markets, it takes years to understand not just the bureaucracy, but how to get the message across, what things you’re able to do, what things you’re able to say, et cetera, and we’re going to be talking about that.

You have a chapter in the book, and I alluded to this before, and this is the one that got me perked up when I saw you speak at Carahsoft at the end of 2023, called Sell, Baby, Sell. Tell us what you cover in that chapter and why you included it specifically.

Nick Sinai: I’m of the opinion, never having been a quota carrier salesperson, but working with many sales professionals and sales leaders and managers, is that sales is an underrated discipline. It’s certainly not the sexy one in elite academic institutions, but it is fundamentally critical to making change. Inside of organizations, at the end of the day, if you’re going to try and make change, and that is get new things adopted, new policy, new product, new initiatives, launch new things, there’s fundamentally a sales process internally that has to happen. In working with sales professionals in my professional life at Insight, and all of the great startups and scale-ups that I work with, I could see so many things about the sales process that applied to making change inside of an organization. I just wanted to bring those two worlds that I live in together and say, “Hey, look, in the discovery, in working through a structured process, in finding ways to communicate the mission or ROI value, how do you tie it to the larger strategic objectives of that organization?”

All those kinds of things, those enterprise selling discipline, that applies to people inside of organizations who are trying to make change too. There’s a bunch of things that your listeners really know and understand of, “Well, how do we decide which opportunities to invest further time in?” One of the most valuable things for sales professionals is their time. Understanding in a multi-stage process where they should be advancing their time and spending their time, because there’s plenty of customers and partners where you can spend time and not actually advance the sale.

The same thing is true if you’re trying to make change internally. You can talk to Joe over in accounting and get Joe all excited about your idea, but if he’s not going to be able to contribute and help and unblock you and help you go forward, you could talk to a customer where you have the technical win all day. Your CRO is not going to care that you have the technical win if you don’t also have the budget win, if you don’t also have the other pieces to that sale. There’s just this element of discovery and a multi-step process and qualification that is very relevant to people inside of organizations who are trying to advance a new idea, a new project, a new initiative, and a new whatever.

Sometimes that is the adoption of technology that is being sold from the outside. There are areas where there’s a nice Venn diagram, but that’s all the chapter was trying to do, was celebrate enterprise selling and say, “Hey, this is relevant if you’re trying to make change,” whether you are deep inside of an organization, or whether you’re a new or an existing executive. My friend Kumar Garg, who I worked with in the Obama White House and who I quote literally in the book, says, “Sales is the one job that you can’t give away in an organization.” The CEO, the executive director of a nonprofit, the secretary of a Cabinet agency, they’re all fundamentally selling for mission or strategic purpose. They’re selling for resources, for investment.

You can give away certain functions like finance and talent and other things, but you have to always be selling as you get to the top of an organization. As Daniel Pink says, “We’re all in sales now.” It’s just important that people respect and understand the enterprise sales process, a true consultative sale that is designed to bring innovative, new capability, and help the customer do big important things. I just wanted that inside of bureaucracies.

Fred Diamond: Anybody who’s in senior levels of government is trying to sell their vision. They’re trying to sell to their constituency. They’re trying to sell to legislators, if it makes sense. They’re trying to sell to their peers, there’s limited budgets, et cetera. I have a question for you. Again, you worked in government, of course, we’re talking about that. Nick, we have a lot of people listening who are sales professionals. They sell for a living. Matter of fact, 80% of our listeners of the Sales Game Changers podcast are professional sales. They work for companies, and that is their job. Give me your thoughts for them.

When you worked for government, what was your expectation of vendors, your expectation of the companies that were providing technology or other solutions to you? I want to break that into two parts. What was your vision or your expectations of large companies? The Microsofts, Amazons, Oracles of the world, and that were your expectations or inclinations for smaller companies, maybe a new company that you might be supporting right now in your life as a venture capitalist. Give us your insights. First, what did you expect of the big boys, the well-known brands, the companies that have been around for 20, 30, 40 years? Then what were your thoughts on, as you were getting approached or thinking about working or bringing into the government as a vendor, companies that were maybe venture capital based?

Nick Sinai: I was a policy official, not a technology official, even though I had this title of US Deputy CTO, and before that was a senior advisor to the US CTO. That meant that I was talking to CIOs and CTOs across the federal government, but my job was also to talk to big and small companies to understand where technology was going, what the issues were both inside the federal government and in important areas like healthcare, and public safety, and education, and so forth. I spent a lot of time trying to talk to not just sales professionals, but also government affairs professionals, and those are essentially the salespeople inside the White House. Those are people who are pushing their ideas because they know that we’re working on a particular policy. They may not think that they’re sales professionals, but they’re fundamentally sales professionals for policies rather than products.

I would make great use of them. I would ask their opinion. I would find out which ones were well respected, which were knowledgeable. I wanted to understand what their knowledge set was, because a great sales professional, this is true of a great government affairs professional, will have a lot of relationships, domain knowledge, expertise. I wanted to try things out with them, and I wanted to talk to people in different organizations to understand, were they telling me the same thing or different things, and why was that?

Then the other thing is you can use them to hack your bureaucracy. It’s funny how you could plant ideas with certain people and they would show up in other parts of your organization because you had said something. I’m sure salespeople are the same way, where they’re saying something and then also having to propagate that across the organization. But I was of the opinion that we needed to have the input, both where the technical vision was going, but also where they thought the limits of policy and regulation. Then I was also very focused on how do we get great technologists to come and serve in government. I was always constantly trying to recruit, both from the big companies, people doing sabbaticals and coming into government or leaving big tech. But then also entrepreneurs were oftentimes willing to have those conversations with policy officials and find ways to contribute to. Our role as the US CTO’s office was to engage both big tech and startup tech, which to include AEs, but frankly, AEs were pretty good at not spending a lot of time with us because they knew that policy officials don’t buy anything and that it was going to be a complete waste of their time. I can appreciate that.

Fred Diamond: When you reached out to technology companies, were your calls returned right away? If they’re getting a call from a deputy CTO of the government, did you find that your inquiries were responded to post-haste, if you will, or sometimes you would have to keep plugging to get a call, if you will?

Nick Sinai: Well, it does help to have the White House behind your voicemail or email. That certainly gets people to pay attention. But look, people are busy inside both big and little companies. It just depends on what you’re trying to do. If you’re trying to see if a CEO could attend an event with the president of the United States in a few days, there’s a way that you phrase that conditionally that’s not committing them to that, but gets the person on the phone pretty quickly, of like, “A very senior official in the White House may want to have a meeting. Would you be able to talk about…?” There are ways to phrase this that people know, but yeah, generally speaking, big brands are great to have behind you. You know the old saw about the IBM sales exec and having that brand on the card, it’s nice to have the White House behind you. It does get your calls and emails returned pretty quickly.

Fred Diamond: You’ve worked in your new role now, or the role you’ve been doing for a number of years in the VC world. You’ve been working with a lot of sales leaders to help them get better to understand how to sell into the federal marketplace. What have you seen, what should they be doing to be more effective in selling their solutions to the government? Once again, this is the Sales Game Changers Podcast. The average listener is selling into enterprise space and to enterprise markets. Give them some advice. What should they be doing to be more effective?

Nick Sinai: I’m going to focus on federal enterprise selling. A lot of these things apply also to commercial enterprise selling, but I’ll just bound my comments. This could also apply to SLED or other markets too. I think that, one, it is very much of a reference game. That is how you get trusted, through mutual introductions. Also, everybody wants to go second. We actually have a chapter in the book about going second. The nice thing about the federal market is that the customers talk to each other. They’re in inter-agency forums. They move from agency to agency. They’re willing to be references if they are excited and a champion of your product or service.

I’m sure your listeners know this, but I would just encourage them to really think about a reference selling. That is in the relationship building and vouching, because this is very much of a trust game, so people vouching for you. But then also, once you have that one flagship customer, how can he or she help you with other customers? That means delighting that customer, not just in the sales process, but in the customer success and delivery, and have that individual, and sometimes those are multiple individuals in that customer, be really excited about you personally as a trustworthy sales professional, but also the company and the product too. Reference selling is big in federal, as I’m sure your listeners know.

The other thing I would say is this is a team sport. It’s a team sport inside of your particular company, of your sales engineers, your customer success, certainly the CRO and the product and engineering people, especially if you have to get FedRAMP or other things, or the federal market. But then it’s a team sport inside of your prospect or your customer. That’s the thing that I hope federal sales professionals take from Hack Your Bureaucracy, is that it is a big, complicated organization that they’re selling to. Your customer is not thinking about you or the category or technology insertion most of their day. There are lots of other bureaucratic processes and systems and meetings and other things that they are dealing with. It takes some activation energy to get things done inside large organizations, and it’s not just about that one person, but it’s actually about probably many people inside that organization.

Helping your customer get unblocked, and sometimes that is having those conversations across the organization, but other times it’s helping he or she be successful. That is the ghost writing, the one pagers, the budget justification, the sole source justification, whatever it is, is doing the hard work to help your customer hack his or her bureaucracy to get the actual sale accomplished and an award to your company.

Fred Diamond: Actually, one of the great things about the public sector market, specifically federal, is that, I remember I worked in Apple’s federal group in the beginning of my career, and I went on a sales call with one of our senior sales leaders. He took me into downtown DC, and I remember he pulled over his car and had me get out, and it was down by the mall where a bunch of the federal agencies are located. He said, “Take a look around.” He said, “They’re not going to knock down these buildings.” He said, “This entity has been around for hundreds of years. It’s going to continue for hundreds of years. It’s a very lucrative marketplace. There’s always a mission, there’s always things that need to happen. Things emerge, things change.” It’s a great market to serve, but I like the way you answered that question, because it’s also a market that you need to understand if you’re going to be successful.

The other thing too is, Nick Sinai, I’ve interviewed a bunch of people who have sold to the federal marketplace their entire career, and in some cases for the same company, companies like Oracle, Microsoft, et cetera. One thing they’ve said is they’ve worked with the same customer for decades. But you got to be careful in some ways, because you can’t give them gifts and certain things you can and can’t do, but they’ve grown up together. The government customer, they want to do their job. That’s one of the things I’ve learned early on is that the typical government IT professional, he or she has a job that they want to do well, and they want to continue to do because of the mission behind it, and how can you, as a sales professional, help them be successful? You know the old adage, help me help you help me help you.

Before I ask you for your final action step, give us a little bit of an insight. Again, you mentioned before, I like the way you said, the average government customer isn’t thinking about you and your technology. There’s a lot of things that they’re thinking about. Give us two or three things that the average government IT leader, the CIO, or director of IT, or ops, or whatever it might be, what are the top priorities that they’re thinking about on a daily basis that sales professionals need to know?

Nick Sinai: They’re thinking about talent more than they’re thinking about technology. They are thinking about how they’re going to build their team, rebuild their team, how they’re going to get talent into their organization. The higher up you go when you start talking to CTOs, CISOs and CIOs, those conversations are much more about the talent than it is any one particular technology. Now, it is incredibly hard to hire talent, and the government hiring processes and all those types of things, but great leaders are always recruiting. Whether it’s inside of their agencies trying to spot great emerging talent, in other agencies, where they might be able to recruit from another agency, or external from industry. They’re thinking about those types of things.

The other thing I’ll say is senior technical or CIO, CTO, CISO types are usually part of the management team, or pretty close to being the management team of an agency. They’re wrapped up in thinking about what is the administration on them for, what are the administration’s priorities? What is the Hill focused on, and what is the Hill beating them up about? What is the crisis du jour, et cetera? All these things that are perhaps not every day IT modernization, which is important, but a multi-year status quo almost. I hate to say that because this is very important and we all need to be investing in modernizing government, but there’s certain policy initiatives, there’s certain crises, there’s certain leadership changes, those kinds of things are going to be top of mind and things that they’re wrestling with that may not be relevant to your particular product or service. One of the things we have in the book is talking about taking advantage of leadership challenges, taking advantage of a crisis, if appropriate, if you can tie to a mission and to solving that particular problem. But these organizations are dynamic and so you just have to understand how they are changing and when they’re changing.

Fred Diamond: Again, you’re working with a lot of technology companies right now that are venture funded, getting into the government marketplace. We have a lot of younger sales professionals listening to the Sales Game Changers Podcast who are in the first couple of years of their career. Do you recommend selling to the government as a career path for them, with your current background? Again, you haven’t really led sales teams, you haven’t carried a quota as you mentioned, but would you recommend that people take that path and focusing on the government as a career path if they want to be successful in sales for their career?

Nick Sinai: I would. You can find examples of people who have been tremendously successful sales professionals, tremendously successful sales leaders, and have gone on to be CROs or CEOs. You’ve seen people who have built entire careers there, and you’ve had some of them on your podcast. The sense of mission. People, yes, they want to be successful and they want to be compensated, but they also want to be involved in important industries. You can think of more important set of missions, whether it is helping the most vulnerable, or protecting the war fighter, or protecting the environment, or whatever the mission set is, there’s just tremendously important missions.

I find it to be really interesting and something that I am compelled to, the complex set of missions and the really impressive people that you meet in government, and some very dedicated public servants, political appointees, uniformed service members. For sales professionals who want a sense of purpose, look, you can go sell large important things in government, but it’s also a complex enterprise sale. Like other verticals that have complex enterprise sales, financial services, healthcare, et cetera, it’s one that requires dedication and mastery if you’re going to be successful as a sales professional.

Fred Diamond: One of my previous guests describes selling to the federal government as the NFL of professional sales. All the great players are there. You got to be top of your game to be successful, but it’s a very lucrative career. I want to thank Nick Sinai for being on today’s Sales Game Changers Podcast. The book, again, Hack Your Bureaucracy, you can find it wherever good books are sold. There it is. He’s got a great website as well. Just go to your search engine, type in Hack Your Bureaucracy, it’ll take you right to his website for that.

Nick, I want to just acknowledge you for the great work that you’ve done in public sector, and also how you’re helping so many great companies right now be successful into markets that you’re working on right now. We’ve had some of your company’s leaders on the Sales Game Changers Podcast as well, and hopefully you’ll help us get some more on the show also. Give us your final action step. You’ve given us so many great ideas, but something specific the listeners should do right now to take their sales career to the next level.

Nick Sinai: Make your customer a hero. You need to have a customer, but too often in our own heads, we’re the protagonist rather than the customer being the protagonist. A lot of people in government get paid relatively similar amounts. For some folks, recognition is important. By the way, this gets back to my earlier comment about reference selling, is how can you tell a great story? How do you have a great narrative about the customer? That customer will tell other people about your technology. People will want to know how they became the hero. Everyone’s like, “We’ve got to get this customer to endorse our technology in our marketing or sales collateral.” That’s great if you can get it, that’s actually pretty hard in federal, but if you can find ways to make your customer a hero, how can you lift up your customer actionably, by saying good things about them, with their permission, feeding information into the awards that are given to federal employees? Those types of things. Help your customer be a hero, because it will help you and your company in the long run.

Transcribed by Mariana Badillo

Leave a Reply

Your email address will not be published. Required fields are marked *