EPISODE 098: Apptio Sales Leader Nick Bollini Offers Strategies to More Effectively Provide Value to Your Customers and Prospects

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Key lessons from your first few sales jobs:
Name an impactful sales mentor:
Two biggest challenges you face today as a sales leader: 13:13
Most important tip: 27:12
How do you sharpen your saw and stay fresh: 33:39
Inspiring thought: 36:54

EPISODE 098: Apptio Sales Leader Nick Bollini Offers Strategies to More Effectively Provide Value to Your Customers and Prospects

NICK’S CLOSING TIP TO EMERGING SALES LEADERS: “If I had to leave folks with one simple thing it’s make sure that you have a purpose, that you know why you’re doing it and that it’s something that you really enjoy doing. Make sure that selling is purposeful for you, make sure you are ever mindful of what is your purpose, and know why you do what you do.”

Nick Bollini is an Area Vice President for Apptio, a leader in the technology business management software space.

Prior to becoming the Area VP for Apptio, Nick spent over 20 years selling IT for companies such as Sterling Software, Mercury Interactive and HP.

Find Nick on LinkedIn!

Fred Diamond: Who specifically in companies do you sell to and what type of companies do you sell to?

Nick Bollini: Great question. What’s interesting from an Apptio perspective is that we have really designed a value proposition that is calibrated to the C suite. In this case it’s really been oriented to the CIO, chief technology officer, often times you get in chief admin officers or CFO’s of information and technology because in many respects the value proposition that our suite of products is oriented towards are there because those personas and their respective teams actually are the consumers of the analytics, the reporting the metrics.

When they look at what their peers in the organizations have and how sales leaders have CRM solutions and corporate finance has their respective general ledgers and ERP’s and even chief marketing officers may have their respective marketing solutions, there really has not been that level of a business management platform for your technology and technology finance leaders and that’s the level of visibility that we have been successfully instrumenting for the last decade or so.

Fred Diamond: Very good. Tell us about you, how did you first get into sales as a career?

Nick Bollini: I “blame” that almost exclusively on my dad. As a food marketing major, there’s not necessarily a real direct translation between the world of food and marketing and that of software selling and so without any real specific prospects exiting college, my pop who’s been a lifelong technology head hunter, he recognized that his son’s only true real gift was talking so he figured that there was a future in selling and so he got me my first gig at a school was in the grind. That is working as a sales development representative doing your cold calling, putting in the sweat equity to drive direct selling efforts for those in the field.

Ironically, the first company which I worked for not too far from here over on International Drive was actually an interesting combination of both the food marketing element – because they were selling distribution logistic software – and the emergence into IT. To think about what we were doing from a selling perspective back in 1994 to where the world has evolved today is pretty interesting but that’s how I got it and I know how to do nothing else other than technology sales.

Fred Diamond: What were some of the first few lessons that you took away from some of those sales jobs that have stuck with you?

Nick Bollini: I think the first thing, the most impactful is just to develop that work ethic to, in some respects, build up the necessary callouses that you need to be successful because a lot of being successful in sales and to do it over the long haul is you’ve got to be tenacious and you got to be stubborn and you’re going to get told no unfortunately probably more times than you’re going to be told yes. You’ve got to develop that level of perseverance, you’ve got to develop that level of tenacity and you just have to appreciate the amount of work that goes into a win. A win can be measured in a variety of different types of metrics but pushing through there.

The other piece that I really took back and it’s a lesson I learned from my friend Kevin McNerney is when you’re in a position no matter what depth and degree it may be is every six months ask for something more, they may give it to you. It could be a broader territory, it could be moving into a different revenue channel, it could be moving upward up the chain of command and if they don’t then use it as an opportunity to get smart about, “What can I do to help myself get to what I’m asking for?” and get measurable objectives that you can re-calibrate your own compass to. I started that in the middle 90’s and I continue to do that today.

Fred Diamond: How would you recommend the Sales Game Changers listening to the podcast today to do that? Schedule a meeting with your boss, formally request more, how would you go about doing that?

Nick Bollini: I think if you think through it in an every six month type of increment, most organizations are going to have your opportunities and your annual performance reviews, biannual performance reviews, things of that nature. I think those of us that have in this game as long as you have been, that the idea is you should be building up a pretty strong rapport with your sales manager or that sort of chain of command so the opportunities are pretty readily available if you orchestrate it correctly.

Fred Diamond: Very good. Let’s talk a little more about you specifically. Give us some insights into your area of brilliance. Tell us what you’re truly an expert in.

Nick Bollini: I think as I look back on my career from an individual contributor perspective what I’ve always embraced are situations where you’re coming into either an under-performing territory that you have to somehow revitalize or it’s with an opportunity to really cultivate a true greenfield where a company’s looking to move into a new market or it’s a small software based type of a firm that’s trying to build out their market.

That’s really what the type of challenge that I embrace where there may be a bit of a trail of tears and you’re trying to resurrect the revenue base or where you’re just seeking a net new opportunity set.

Those attract me the most. I also think that one of the national areas that plays to how I sell, personality and so forth is this idea of being highly accountable in your sales efforts and what that tends to lead to is the ability to capture a new customer and then find ways of driving repeat opportunities to engage them. If you lead with the value orientation, if you set a long term vision then they’re going to begin to look at you as a trusted partner, not just as a vendor. Being able to sustain that kind of base allows you to institute some levels of predictability in an otherwise fairly unpredictable line of work from a software selling perspective.

Driving that repeat business, building on those incremental successes you tend to find that you’re able to establish a really valuable champion and a really strong reference that you can go to over and over again but you also start building out a strong base of business that you yourself can refer back to and capture revenue on a quarter by quarter, year by year basis.

Fred Diamond: Very good. You mentioned your father, you mentioned Kevin McNerney who’s a very successful recruiter in the area. Tell us about a sales career mentor and how they impacted your career.

Nick Bollini: The easy answer would be my pop. He was the first to help orient a life of selling into the idea of never get too high, never get too low, the more you can stay even keel the longer you’ll have in this particular space.

But when I think back in terms of sales leader that whether it’s two years from now or five years from now or even the present tense, the current chief revenue officer of Apptio by the name Larry Blasko is the guy that I look to in terms of his ability not only to lead an unbelievably successful sales organization but the way in which he drives his sales teams, the way he really instills motivation that can be personal in nature is just spectacular. It is what allows for me, a guy who’s reported to him for seven years, to still go back to and want to perform – obviously for myself – but he makes you feel like you’re part of something bigger and I think that’s a whole different type of culture to drive results.

Fred Diamond: What are the two biggest challenges you face today as a sales leader?

Nick Bollini: I think the first one that’s probably really apparent is hiring. Hiring, retaining and enabling sales talent. My team is pretty spread out across the east over from Eastern Canada all the way down into the southeast areas. There are certainly pockets where you’ve got a really deep pool of talent and folks you can pull from and others that are perhaps a little more shallow, just to be really mindful of that. You also have to begin to understand what attributes of a candidate play well.

Just because someone has been successful in their career doesn’t mean they’re going to be a good fit in your particular organization so you’ve got to start figuring out which of those dimensions you’re going to value and that’s just the starting point. You’ve got to identify those candidates, you’ve got to then sell the opportunity and you want to find those folks that think the opportunity is right and then you got to bring them in and you got to enable them and it’s really your responsibility – at least I view as my responsibility – is to invest in the person.

Make them as enabled and as convicted as possible because the faster you can shrink that time to productivity, the faster you can get results and you want that kind of buy in. We’re very focused on keeping and developing our sales culture and ensuring that the talent stays with the firm. That’s really what catapults your growth.

Fred Diamond: Just a quick comment. You’re episode #98, we’ve done a couple special episodes so essentially you’re episode #103. We ask that question every single podcast, what are the two big sales challenges. #1 by far is hiring, retaining, motivating or enabling top tier sales talent so I’m just curious, how much of your time do you think is spent interviewing, recruiting, seeking, going up on LinkedIn, getting referrals for people who may join your team?

Nick Bollini: It’s seasonal in some respects. There is always that mantra of always be recruiting just because you want to be mindful of which types of folks are out there. I’d say a decent amount of time is there and fortunately for us, we’re blessed with having an internal recruiting contract here at Apptio that I will feed and be proactive with them and say, “Here’s some markets that I want to be looking into” or “Here’s someone I’ve come across” and begin that soft recruiting positioning of Apptio. It’s not an insignificant amount of time that you dedicate to that type of program.

Fred Diamond: Before you give us your second challenge, do you ever get approached? How often do you get approached by people via LinkedIn or something like that aggressively on the sales professionals such as the people listening to the Sales Game Changers podcast about possible employment?

Nick Bollini: There is a pretty deep queue of LinkedIn messages on all different sizes, folks that are interested in Apptio, folks that have other opportunities that are there, it’s a pretty regular basis, it’s out there and if you’ve been doing this long enough you know that the name gets around and people begin to understand who people are. Folks you worked with before get to a new place and the first questions comes up is, “Hey, do you know someone in this particular market?” and that opens a door to another two to three more recruiters that come in and there’s a pretty steady stable of folks.

It’s a fairly regular basis, I don’t think it’s any kind of exaggeration to say that it’s a daily occurrence in some form or fashion. I do my best, I try to be a respectful employ to the inquiries but to me I try to tune out the white noise. I have a mission and I do not want to be distracted.

Fred Diamond: Now that your Sales Game Changers podcast episode is aired, expect that to increase.

Nick Bollini: Fantastic!

Fred Diamond: You also had a second challenge?

Nick Bollini: I think for me, good advice that happened is obviously most managers are from my perspective first getting into sales management you’re moving out of the individual contributive role and into the management and they gave me this advice around the foxhole analogy is you’ve got to let your team dig the foxholes. They want to know that you are with them and you have their back, you support but if I had to identify an area that I continue to struggle with – well, I wouldn’t say struggle with but that I’m conscious of getting better at is learning, and it’s more art than science, learning when you need to differ and delegate and let the rep run the route and when you need to stand in and serve in that leadership capacity to help them advance on their goals because you can’t close every deal for them.

That’s why you hire well, is because you’re hiring a team of professionals to go about and do their due course but they need to know that they’ve got the support. Especially when you’re coming from situations where you yourself may have been that individual contributor, you may have been that particular rep, it’s easy to fall into the natural, “Well, I would have done this this way” or, “Gosh, why don’t you do that and you bail play, you play armchair quarterback and that just doesn’t create a real healthy relationship.” I would be lying if I said I was a master of that, it is definitely something that I work very hard at to get better.

Fred Diamond: That’s pretty powerful. As I’m thinking about some of the past episodes, one that comes to mind was Scott Attman who works at Acme Paper and Supply. He talked about one of his transitionary moments being the time that he went on the first big sales call by himself and that the sales VP who he had been going with on every call just said, “Take it, it’s for you” and talked about how much of a transitionary and transformational moment that was for him. Nick, take us back to one specific sale success or win from your career that you’re most proud of. Take us back to that moment.

Nick Bollini: I may double down and do two quick ones here for you, Fred, because I think it’s important to talk about the context of a win as a rep and perhaps a win as a leader from a management perspective. I think that one thing that’s interesting is there was a particular deal – I’m not to name names, but a very large not for profit base right in the heart of Washington DC – and we were competing against a variety of other, at that time, fairly commodity oriented operations and manager software. It felt like there were a hundred of them at the time and trying to find ways to differentiate yourself.

We felt pretty convicted about the solution that we had offered and it has a significant dollar figure associated too but what’s really interesting is not only the competitive win and the strategizing at an exceptionally good technical engineer that ran point with me, but it was the first time I realized the differentiating value that the cloud and the notion of as a service could really provide organizations and that has obviously been proven true as the next decade plusses has folded in and what organizations that were first movers into that particular way of delivering their solution and also employing a managed service could really establish themselves against organizations that have been around for decades there.

That was a differentiator that was hugely compelling for the client and in some respects it justified a price point that was potentially thirty or forty percent more than the competitor but because they viewed what we had as a term key and that was great. That began to orient myself to a more value based selling, don’t sell the features, sell to outcomes.

The second thing, the other deal was from a management perspective was just there is a massive financial orientation, the backbone of the United States financial management system and they were pushing us to deliver into areas that we were not necessarily comfortable delivering before so when you start thinking about the notion of serving leadership and how you want to go and provide that level of air covered for your rep, being able to find ways to instrument other areas of your company to come together and in some respects push themselves out of their comfort zones to deliver on a solution, deliver on a delivery, commit to certain levels of accountability that we were not ready to do but we were willing to do in order to secure the business helping to lay that down and helping the rep understand that.

That was my job, his job was running the deal, my job was to get him the support he needed to sell successfully. That is really why you get into leadership, is to move beyond the impacting of yourself and impact to the many.

Fred Diamond: Absolutely. Again, this is the Sales Game Changers podcast, my name is Fred Diamond. We’re talking to Nick Bollini. Nick, before we go to break and listen to one of our sponsors, sounds like you’ve had a great career in sales. You’ve obviously been very thoughtful about the process, you’ve worked for Apptio you said seven years now?

Nick Bollini: Seven years.

Fred Diamond: Seven years, you’re now the area VP, you’re bringing great solutions to your customers. Of course, you’re a food marketing major, could have gone down that route, if you will. Also, you said you went to St. Joe, right?

Nick Bollini: Saint Joseph University, Hawk Hill.

Fred Diamond: We could talk about Philly all day long, here.

Nick Bollini: That we could.

Fred Diamond: [Laughs] did you ever question being in sales? Again, your father after you graduated with your food marketing major, he said sales makes the most sense for you. Was there ever a moment where you thought to yourself, “You know what? It’s too hard, it’s just not for me”?

Nick Bollini: Every last week of every quarter, Fred, I would say that that goes through the back of your mind. It’s a hard business, it’s a grind and there are a lot of different dimensions. When I think back as to why have I stayed in, you enjoy it. You have to be right for it but it is hard and if it wasn’t then everyone would get into the game. You really have to rely upon your own support structure, having a wife that is understanding of the travel, of the deadlines, of the pressures that are involved there makes it manageable and I don’t know how I would do without that but you just have to create your own – I guess the best way to frame it is you have to be able to embrace the lifestyle in many respects.

The selling side of things, and some don’t turn off. It’s an always on kind of business and it’s hard.

Fred Diamond: Especially when you’re in sales management. You have people underneath you, you have constant pressures from the inside and from the outside, it doesn’t go away so you do need to be focused but it sounds like you’ve also done a great job balancing your home life, you have four kids.

Nick Bollini: I try, it’s always subject to debate and based on the time of year and which kid you ask but yeah, I think you have to be mindful of that. I think there is a work life balance and if you ignore one or the other things tend to not go the way you’d like them to go.

Fred Diamond: Nick, what’s the most important thing you want to get across to junior selling professionals to help them improve their career?

Nick Bollini: I think the first thing that I would suggest is stay humble. Those that are seeking in the trenches of this career, it should never be about you. I think those that are not willing to take guidance, those that aren’t willing to learn the examples of others, those that develop that ego and live and sell beyond their means, they aren’t as successful as they could be and that’s a lesson that I learned early on and I’ve perpetuated it down to hopefully the way my team knows how I manage and what I look for them to operate on.

I think if you sell humble and keep the customer front and center versus your own self needs then I think you’ll end up being in a much better spot. I think a lot of it is it’s easy to say you should talk less and listen more, that’s assumed but when you do talk, speak simply. The more simple the questions, you’ll be amazed at what actually you can extract from a client if you start to think about what else, or ask why or when or who or how. You’ll find some pretty intriguing questions and I can guarantee your sale cycle will advance at a far faster clip if you let the customer tell you the information you want versus you just trying to guess and assume.

The third thing I would say is in this day and age with the rate at which technology is being devoured in which new products coming to market spend more time orienting yourself to the outcomes that the prospect or client is looking to achieve versus your own features. There’s a term that I always like that’s, “Don’t talk about the dog.” No one cares about the dog, they want to talk about themselves. Let them tell you what they’re trying to do with your set of capabilities, that’s how they build value, that’s how they’re going to calculate the rate of return for investing in your solutions. If you spend more time talking about feature function, you’re putting yourself into you’re just another vendor versus that enabler that’s going to get them to the objectives they’re trying to seek.

That’s what I would sell to you, focus on outcomes, not features.

Fred Diamond: That’s very powerful. What are some things you do to sharpen your saw and stay fresh?

Nick Bollini: For me it’s kind of a read, refine, and reload sort of mantra. I wish I had more time to read and I try to be selective about the books that I do read but there’s a lot of really good ones out there. I just finished a book called Grit by Angela Duckworth which was fantastic. Don’t bury your library with a bunch of business oriented books, but that’s always a great source to give yourself different perspectives, especially when you can find those that provide really good selling examples, that definitely helps.

Refine is really more about hopefully you are working for a company that promotes the idea of improvement and they make the investments. There’s always new selling strategies, there’s always new types of tools and methodologies that you can go back to even if it’s just from a reminder perspective. Invest the time to hone your craft in that area from a sales skill perspective. Finally, the reload is most software companies are going to have a wealth of information they make available.

Spend the time in figuring out customer use cases, watch the videos that are created, understand how your customers are using your software, understand the white papers that are written, consume those assets that are made available so you become a domain expert in the where’s that you are bringing to market because again, you want to find ways of differentiating yourself from those that you are competing against and if you are able to combine that blend of sales acumen with domain understanding then that’s how you establish yourself as a trusted partner versus a vendor.

Fred Diamond: Very good. What’s a major initiative you’re working on today to ensure your continued success?

Nick Bollini: I readily seek opportunities inside my company to be part of product advisory, swat teams, figuring out how can we package differently, how can we insert and address new capabilities based on what we’re observing in the market. Those are things that I continually try to do. Frankly, my biggest initiative, Fred, is moving into more of a manager of managers type of a role and fortunately I’m blessed with a company that has given me the opportunity to move up the chain of command as it were and building out and scaling a team to help drive the company to the growth objectives that we have.

That’s my new personal initiative that I’m taking on is OK, how do I do that well? Doing in some respects your own swat analysis, where am I strong? Where am I weak? Where are the opportunities and what in my own bag of tricks do I need to maybe put aside that can be a threat to being successful in that endeavor? We’ll see how that plays out.

Fred Diamond: Good luck on that.

Nick Bollini: Thank you.

Fred Diamond: I’m sure you’ll succeed. Sales is hard, Nick, people don’t return your calls or your emails. You’ve given us some great insights into how you manage and how you’re looking to grow as a manager but why have you continued in sales? Help us understand what it is about sales as a career that has kept you going.

Nick Bollini: Sales is a game. The bottom line is if you’re not competitive then you’re probably in the wrong line of work. That is what keeps things fresh for me, the life of a sales professional is dynamic in nature. Very rarely do you have weeks that look the same, you are always at task with a new challenge, quarter over quarter you get to engage with new and different people, you’re out solving and being presented with new problems that they’re seeking to solve for. Especially in the IT space the way that things are changing and the trends that are being emerging and you’ve got to adapt and adopt, that’s fun.

That to me is really what is, frankly, still exciting after over two decades in the space. I think from a sales leadership perspective when we talked a little bit about it earlier in the podcast is you’ve got to make a conscious decision to move out of being an individual contributor where you’re focused on you and your own personal achievement. You move into that space of how can I take what I know and have a positive impact to a team and being mindful of their success and the goals that they’re trying to achieve and how they’re trying to provide in their respective worlds.

That is what I really enjoy and in our sales teams we’ve got all folks in all different walks of life and some folks have families, some of them just got married, some are on different stages of life and they’re all trying to manage their own goals, objectives and their ability to earn, their ability to advance their own careers is part of what I’m trying to impact that it’s no longer just about me. It’s about how do I give them a good experience in this particular case and selling in Apptio, being successful in Apptio and that is 100% what keeps me engaged and excited about selling.

Fred Diamond: Nick, bring it on home, give us one final thought to share with the Sales Game Changers listening around the globe today.

Nick Bollini: From a point of inspiration I started thinking about what inspired me – something I could look to in the last couple months and I mentioned earlier this book I finished reading called Grit and one of the chapters starts off with the parable of the brick layers. The story is such that a traveler comes across three brick layers and the traveler asks the first brick layer, “What are you doing?” and he says, “I’m laying bricks” and then he goes and asks the second brick layer, he says, “I’m building a wall” and he goes to the third brick layer and he says, “What are you doing?” and he’s like, “I am building a cathedral.”

The first person has a job – hey are laying bricks. The second person – they have a career like I construct walls and the third person has a purpose, they have a calling and he sees that the means to an end is I’m building this cathedral.

That’s what I would encourage those that are listening is make sure that this is your purpose, make sure that selling is purposeful for you, make sure you are ever mindful of what is your purpose, why do you do what you do, it’s hard, it’s a hard line of work and you have to think through because you’re getting on red eyes, you’re going from why are you doing what you’re doing. To have that in the back of your head drives you.

The third thing you want to think about is make sure you work for a company that you are purposeful and supporting. That’s how you get out of being in a career, that’s how it doesn’t feel like it’s a job. You’ve got to be thinking about what am I trying to achieve, it’s more than just me, I’m working hard because I’m trying to create a market, I’m trying to take something public, I’m trying to do whatever it may be and so working in an environment that fosters that kind of a culture allows you to really orient yourself to the purpose of what you’re trying to do. If I had to leave folks with one simple thing it’s make sure that you have a purpose, you know why you’re doing it and that it’s something that you really enjoy doing.

Transcribed by Mariana Badillo
Produced by Rosario Suarez

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