EPISODE 151: Cvent’s Alex Rolfe Said Taking this One Big Risk Propelled His Sales Leadership Career To New Heights

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EPISODE 151: Cvent’s Alex Rolfe Said Taking this One Big Risk Propelled His Sales Leadership Career To New Heights

ALEX’S FINAL TIP TO EMERGING SALES LEADERS: “Time how much you speak on a demo. Are you speaking for 70% of the time and the prospect is speaking for 30%? What can you do to speak less and let your prospect or your client speak more? What can you do to listen more?”

Alex Rolfe is a senior director for event solution sales at Cvent and been with Cvent for 13 years holding various sales and sales leadership positions.

He is the third person that we’ve interviewed from Cvent. We’ve interviewed Darrell Gehrt, the VP of Sales for Cvent Mobile and Brian Ludwig, Senior VP of sales for the company.

Find Alex on LinkedIn!

Fred Diamond: I’m excited to hear your story today. Cvent is a great success in a lot of ways. Tell us what you sell today, Alex and tell us what excites you about that.

Alex Rolfe: Cvent is an event technology company, so we sell a platform of solutions that allow event organizers to provide a fantastic experience for their attendees as well as drive operational efficiencies and at the same time help to prove the ROI of their events. We’re selling a whole platform of solutions, everything from registration to mobile apps to onsite solutions for checking and badging. I think most folks probably don’t realize everything that goes into an event, certainly an event planner does and it’s a very challenging job, it’s incredibly exciting to be able to speak with them and uncover some of the challenges that they’re facing and how our technology can really help them and help elevate their careers within their organization as well.

Fred Diamond: How did you first get into sales as a career?

Alex Rolfe: Interesting story, they’re probably not the same path that many of the other folks you’ve spoken with have taken. My passion started with events so we talked about sports a second ago, I was always fascinated with how events brought people together. I remember going to events at Madison Square Garden and watching UConn versus Syracuse, I think was the first game that I went to. I don’t remember who won the game but I do remember the scene and the setting, and just how passionate everybody was that was there. I think from there it led me to follow down that path of events can really bring people together and drive these connections so much so that running Madison Square Garden was my dream job if you asked me what I wanted to do. I ended up going to the University of Massachusetts, graduated from their business school and then pursued a career in event management.

I was an event manager for several years out of school, and then I started to get more involved in the production side of events seeing how technology impacted it. At that point I came across a small company at the time named Cvent, and was really enthralled with what they were doing and their vision for how technology can impact. This was obviously not consumer events but B to B events and joined on board, this was May of 2006, the company was about maybe 75 people at the time and I’ve been there ever since.

Fred Diamond: Alex, talk about your passion for events, I like the way you said that, and talked how that has helped you become a successful sales leader.

Alex Rolfe: I think it means a lot, I think you have to have passion about what you’re selling no matter what it is. When I made that decision that I was looking to change my career, after being in that event manager role running Madison Square Garden quickly became not my dream job after getting that insight too. Again, I did have that passion for events. I think once I knew that and as I started to look what was out there in the market, I actually heard of Cvent from some of the clients that had actually come to our building to rent meeting space. I think it was mutually a great fit at the time, but it was my first entry in sales.

As I came down and interviewed with Cvent, I knew I wanted an opportunity with them and moving into sales made a lot of sense. Cvent, I think, was pretty early with their SDR program and this was 2006. They had a pretty decent SDR program in place at that time so it was also a place that I knew I could step in and learn how to sell. That was something that was very attractive to me as well, looking to make that change in career path.

Fred Diamond: What were some things you learned? What were some of the lessons you learned from some of those first few sales jobs?

Alex Rolfe: My first sales job was at Cvent as an SDR and I think what I learned the most was that we were calling folks and talking to people and at that point we were really trying to get them to use online registration. It wasn’t this broad platform that we had today, it was a single product that has since evolved from there, and I learned that people have a tremendous amount of pain. We think about the opportunities that our solutions have to help them not only as an organization but also as individuals, and I think it was the individual part that I learned the most in that SDR role is how can our solutions help that individual and impact not only their day to day but also help them grow in their career because if they brought something like Cvent in and were successful with it, that would reflect really well on them.

Fred Diamond: We talked about events, the next question we usually ask is “tell us what you’re an expert in, tell us about your area of brilliance.” I shouldn’t answer the question for you, but it probably has something to do with events.

Alex Rolfe: It does, I think I’m incredibly strong in relation to events is really events and event marketing and the impact that events can have on a business. I think a lot of folks look at events as a call center often of yes, it costs money to rent our events but why are we running them? What’s the outcome that we’re trying to achieve? What’s the ROI that we’re looking to gather, why are we spending all this time, effort, energy and money to produce an event whether it be a user conference, whether it be a sales kick-off meeting, whether it be a meeting for our customers or our prospects?

A lot of effort goes into that, so helping organizations really understand and identify, and sometimes they forget what’s that core purpose of our event, all the pieces of technology that we need to hook to align with it as well as what’s the business outcomes that we’re trying to achieve and then how do we measure it. I think that’s probably where I would call myself the strongest from an event sales standpoint.

Fred Diamond: I have a quick question for you. Again, before you came to Cvent you were managing events, you’ve always been fascinated by events like you talked about and of course you said your area of brilliance is events and events marketing, but I presume a lot of people who came to a company like Cvent didn’t have that background. Either they came right out of college or they had another job before they got here, before they took an SDR or one of those inside sales roles. Not just Cvent, but what would you recommend obviously knowing that and understanding the operations of your customer gave you an advantage to be successful in selling to the audience that you already knew? What would be some things you would recommend to the people listening to the podcast to get that knowledge if they didn’t come to the job with that knowledge?

Alex Rolfe: I think it’s just having a deep industry understanding, there’s a lot of ways that you can get that. While I had that passion for events, I didn’t understand the B to B events industry when I joined it, that was completely different. How does a corporate event marketer work? How does an association event manager, what makes them tick? What are the challenges that they face? Somebody who’s running events at a nonprofit is very different than somebody who’s running events at a state government agency. Being able to understand that buyer persona, being able to understand the industry, who the key players are, competitors, I’ve really tried to immerse myself in that and I do that to this day because it’s constantly changing and evolving.

I think regardless of what industry it is, regardless of whether you think you know it when you move into it or whether you move into a new career and a new vertical, I think just taking the time to deeply understand it is probably the most critical aspect of it so that you can have educated conversations with your clients and prospects. Without that, they may have the upper hand on you because they’ll know more about the industry than you do. I think being able to position yourself as an industry expert even more so sometimes than your product is important.

Fred Diamond: Tell us about an impactful sales career mentor and how they impacted your career.

Alex Rolfe: Probably the most impactful mentor of my sales career was on your podcast, Brian Ludwig. I’ve worked for Brian my entire career at Cvent, so certainly he’s somebody that I’ve learned from, that I’ve looked up to. Our career paths have always been intertwined here in a very positive way. When I started at Cvent, Brian was a sales executive and I was his SDR, and then as Brian continued to move up, he became VP of sales and then an SVP of sales, when he needed help I was somebody that he turned to.

We haven’t had a sales manager on our team prior to Brian moving into a VP role, he was doing that as a director/sales executive and then we had a VP of sales that Brian reported into but as we grew, the need for Brian to run this part of the organization opened up that opportunity for him. It also opened up the opportunity for me to come underneath him as a sales manager and he’s certainly taken up more responsibility over the years as have I. Our careers have always been aligned and I’ve always looked to him for guidance, leadership, mentorship, the ability to bat ideas off him, good and bad. I think we’ve done a lot of good things, we’ve certainly made some mistakes along the way but I think having a mentor that I’m able to work so closely with, that I understand well and he understands me has been a very strong part of our mutual success here at Cvent.

Fred Diamond: Of course as a sales leader there’s a lot of challenges that you face as well. What are the two biggest challenges that you face today as a sales leader?

Alex Rolfe: I think one of the biggest challenges that we face in my team specifically is our platform is quite complex, so how do we take what can be a complex platform and sell it and simplify it to our buyers? Because they have a lot of challenges and we have a lot of solutions for them, but how do we take a broad ranging platform set, boil it down and show our prospects and buyers that they can easily adopt, implement and be successful with our solutions. Beyond that, I’ve thought about a couple other challenges that we face. It’s about getting the right leads to our team at the right time, so how can we leverage a lot of new technologies that are out there? I wouldn’t call them new anymore, but ABM, AI, lead scoring, what can we do to be smarter about the leads that our team is getting versus just sending them a list and saying, “Start calling”?

Fred Diamond: Cvent’s had a great run. You must have had some great successes along the way for the company to have gotten to this point, why don’t you take us back to your #1 sale success or win from your career that you’re most proud of?

Alex Rolfe: Most proud was my first year as a sales manager that my team had budget. I think that was probably the most proud moment because it was the first time that I got the opportunity to feel what it was like to be a leader and to hit that number as a leader versus an individual contributor and see what it took to motivate, inspire and work with our team in order to get there. I think hitting budget every year is a challenge as it should be, but that first time I think was pretty special.

As an individual contributor I’d have to go back to 2008 in the recession, that was probably a challenging time for a lot of folks that were selling then and we were able to close some pretty significant deals with some pretty significant enterprise organizations during that time. I was most proud of that because we were selling a solution that wasn’t fully ready at the time, but they were aligning their vision and their goals to where our product was going. I think at that time during the recession being able to work with them, we had to be able to show that our visions were aligned together and that if they were placing their bet on us that it would pay out for them in the long run, which it has.

There were two particular customers I’m thinking of when I say that and we’re almost 10 years past that, both of them are still customers today doing extremely well and their event programs have continued to flourish.

Fred Diamond: Again, we’re talking to Alex Rolfe today. Alex is the senior director for event solution sales at Cvent, he’s been with the company for 13 years. Talking about some of the successes he’s had along the way. Alex, as we mentioned in the beginning, you were an event guy, you loved events. One of your passions was to one day run the Madison Square Garden and then you moved into sales. You’ve had a great mentor, you’ve had a great run, Cvent’s a growing company. It’s a lot of energy, we’re doing today’s Sales Game Changers podcast from the sales floor at Cvent. A lot of energy, a lot of people on stand-up desks, everybody I’ve noticed has two monitors and there’s a lot of buzz, there’s a lot of interesting high energy people here today. You made that shift from events into sales, did you ever question being in sales? Did you ever think to yourself, “You know what, Alex? It’s too hard, it really isn’t for me”?

Alex Rolfe: Truthfully, no. I’ve loved it from day 1, I think the competitiveness of it has always brought me to it. Frankly, I think in my previous career I didn’t like the fact that while it was a lot of hours, it was a slower pace and there wasn’t as much of a challenge. It was very similar day to day, so I was looking for a change of pace and something that did operate at a different speed and that would challenge me intellectually more than what I was doing in the event manager role.

Just from day 1 moving into sales I was absolutely motivated by it and I think a lot of it came back to not feeling that we were going in with a product that wasn’t ready for our buyers or that wasn’t ready for the market. It was ready, there was a clear challenge in the market and we were building and developing solutions and had them in place that helped them solve those challenges. It was just a matter of we’ve got a great story to tell, what can I do to get in front of the right people to tell our story? Once we do, I felt very confident that there’d be at least an opportunity for us to do business together, but of course getting in front of somebody to tell that story is not always easy as well and that’s where I think a lot of that energy and action and passion really comes into play.

Fred Diamond: It’s also great to be working with a company that’s doing well, a company that’s grown over the last two decades and has really become the leader in its space and is a place where people want to go, with nice, bright, attractive people who want to come work here.

Alex Rolfe: It is, and that’s been a hallmark of Cvent for quite a while. There’s certainly other companies out there like that too. As I think about my career and I think about Cvent, you of course always have the opportunity to grow your career internally or to look at other opportunities externally in order to do that. I think for my career path I’ve been fortunate where every several years where I felt I was hitting a ceiling, that ceiling was raised because of the growth that we were having here and the opportunity for new challenges.

Also, if you are in a growing company, that company is changing quite often. When I started we were a private company, we went through some several significant funding rounds, we went public, we were public for several years, we became private again. Even being at a company for 13 years hasn’t been the same, it changes in ownership, changes in strategy, product development. I would say if anybody has that opportunity to grow within an organization, it gives you that opportunity to experience new challenges along the way. The challenges I face today are very different than the challenges I faced even a couple of years ago as we continue to grow.

Fred Diamond: Alex, what’s the most important thing you want to get across to the junior selling professionals listening around the globe to help them take their career to the next level?

Alex Rolfe: One would be to take risks, and especially take risks early in your career. I remember when I had the opportunity to move from an SDR role to a sales executive role, it was me and one other person at the time and we were with our CEO and we were looking at territory, who’s going to get what territory. I had the option of getting a bunch of states in the US, North Carolina and Illinois, Massachusetts or whatever they were at the time or I could have taken a few less states in the US and also try to help grow our business in the UK and Europe which we didn’t have presence in at all, but we knew we wanted to start trying to sell there. I immediately raised my hand and said, “I want to do that” and it was probably the best thing that I ever did.

It was challenging, if you think about it from a personal standpoint I probably made 20% of my earnings selling into the UK and Europe but I probably spent 50% to 60% of my time on it, but it helped me as a business individual to grow my acumen, understand a new market, understand how to sell to a different market while at the same time being able to sell in the US. I also had a chance to travel there a couple times a year to meet customers and do presentations, and I think that opportunity helped me to the point where I am today, but I could have easily just said no.

Fred Diamond: “Give me the gravy accounts.”

Alex Rolfe: “Give me the gravy one where I know it’s there, it’s proven, it’s going to work” but I didn’t and there were challenging times but it was absolutely the right decision. Anybody who has an opportunity to take a risk early in your career, put yourself out of your comfort zone, it will pay off in the long run even if it doesn’t potentially pay as much in the short run.

Fred Diamond: I’ve had a couple jobs in my career where I’ve done international travel and great experience. I reflect back on a lot of those trips and what I’ve learned, being able to just meet different people really gives you a richer understanding as you grow your career. I urge the people listening to the Sales Game Changers podcast, take those risks, take an international job every once in a while, it’s going to definitely change your life.

Alex Rolfe: It might not even be international, it could be a different vertical that your company is not in today or just a different market that they’re trying to get into. Take that risk and you can become the leader and the expert in that, in whatever it is, international, vertical, etc.

Fred Diamond: Lead your company into some new markets, that’s a great idea. What are some things you do to sharpen your saw and stay fresh?

Alex Rolfe: I read a lot, I want to make sure that I’m up to date, what some of the trends are out there, I read a lot of biographies and nonfiction, I like to learn from other leaders both internally and externally so as Cvent’s grown we’ve brought more external leaders in as well. Sometimes it’s as simple as saying, “Let’s grab a cup of coffee, let’s go downstairs, I’d love to pick your brain about how you approach sales at whatever company you came from before.”

As somebody who’s been at Cvent and really grown my career here, I want that outside perspective. I want to be able to take in what some of those best practices are that somebody else might be bringing to the table as well as internal folks that we have here. Then I mentioned it earlier but I subscribe to a lot of blogs, both sales blogs like yours and others, I listen to a lot of podcasts and I’m following a number of websites both for sales knowledge but also to make sure that I’m up to date on our industry trends, what our buyers are thinking about and then I also pay close attention to our competition, what are they doing. Those are just some of the things I’m doing to make sure that I’m staying fresh.

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

Alex Rolfe: One of the things that we’re thinking a lot about is verticalization. We sell into a variety of different verticals, you have the opportunity as you grow to potentially segment out those verticals and get a little bit more focused on it. For example right now we’re planning out how to focus more specifically on our higher education vertical and what are some of the specific needs that higher education needs that might be different from others and what should our go to market plan be as we want to continue to grow in the higher education space. That’s an area that we’re thinking about as well as just being able to get more scientific, I would say with our approach to lead scoring and delivering the right leads to our sales team.

Fred Diamond: Alex, again you moved from event management, event marketing, you ran some event venues and of course you moved into sales. Sales is hard, there’s a lot of challenges, of course you told me you made a move to covering the international space and all the things that come with finding new markets and building those and getting a territory that’s tough but eventually you succeed. People don’t return your calls, they don’t return your emails, why have you continued? Again, you made that shift 13 years ago when you came to Cvent. What is it about sales as a career that has kept you going?

Alex Rolfe: Every day is different, being able to wake up with a new challenge every single day, being able to know that there’s a whole bunch of folks out there that we haven’t even spoken with yet that need our solutions and thinking about how we can get in front of them, how we can educate them on what we do. Then once we have the opportunity, it’s really about learning about them. That’s my favorite part of it, is how can we get in there, how can we talk to organizations, learn about the challenges that they’re facing and be able to provide a solution that’s going to bring tremendous value to the organization.

As I look ahead, I think one of the exciting things about sales is the not knowing and if you’re at an organization that’s evolving and changing and developing new products, it’s not static. It’s also just not having that crystal ball of where you’re going to be three to five years from now, that’s one of my favorite things about sales, especially about sales at Cvent.

Fred Diamond: You’ve given us a lot of great things to think about, we have Sales Game Changers around the globe that listen to the podcast, why don’t you give us one final thought to inspire them?

Alex Rolfe: I’ll go back to what I said earlier, take risks, that’s #1. Think the more that you can take risks, and that doesn’t mean just international or anything like that, it’s challenging yourself thinking about what your weaknesses are and focusing on them.

I’ll bring it back to a sports example, I was a basketball player growing up, I was too scrawny to ever make it beyond high school but man, could I shoot a basketball. I still can today, I could pour in points like nothing else but I couldn’t play defense very well so I remember going into my junior year of high school saying, “I can score, I know that. My shot’s not going anywhere, I’m going to spend a little more time focusing on my defense and really trying to work on my footwork and where I need to be and make that a point of emphasis.” I became one of the best defenders on our team where I was matching up with the other team’s leading score on the other team and trying to shut that person down.

I think about that from a sales standpoint as well of what are areas that you need to improve on? We have our strengths and I think those are great, but more importantly what are our weaknesses and what can we do to focus on those to really improve our skills?

Fred Diamond: Alex, not everyone listening to the podcast is going to have the opportunity to break into international markets for the company. As we close down here, just give us one risk. Give us one thing that you’ve seen that you challenge your people with, one simple out of your comfort zone type of thing that you would recommend to the Sales Game Changers listening today.

Alex Rolfe: How much time they speak on a demo, really make them time it. How long are you speaking? Are you speaking for 70% of the time and the prospect is speaking for 30%? What can you do to speak less and let your prospect or your client speak more? Part of that is simply being quiet sometimes, asking a question and letting somebody respond. I think the easiest thing to do is we want to talk so much about what we do because we have so much to say, but getting someone to open up and talking, letting them speak on the call is something that I really like to challenge my team with, so very easy thing to do. What can you do to listen more?

Fred Diamond: Listen more and talk less.

Transcribed by Mariana Badillo
Produced by Rosario Suarez


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