EPISODE 003: PowertoFly Sales Leader Caroline Turner Speaks About How Women in Sales Can Achieve More in Their Career

EPISODE 003: PowertoFly Sales Leader Caroline Turner Speaks About How Women in Sales Can Achieve More in Their Sales Career

Episode 003 of the Sales Game Changers Podcast went live on October 1. We interviewed Caroline Turner, chief revenue officer for the start-up PowertoFly, a diversity talent platform. She oversees sales and customer success and is preparing this three year-old startup for its next round of funding by putting in place a repeatable revenue process. On the podcast, she shows how passionate she is about understanding the buyer and delivering products that are easy to buy, are easy to use, and meet an urgent market need. She discusses how to effectively participate in all aspects of the sales process including getting into the weeds and understanding each step of the buying process, training sales teams how to close deals and run sales calls. She also discusses how to set the strategic goals for the revenue teams.

Find Caroline on LinkedIN!

Here’s a transcript to the podcast:

003, PowertoFly’s Caroline Turner

Fred Diamond: Very, very excited to be talking today to Caroline Turner. Caroline is PowertoFly’s chief revenue officer. She oversees sales and customer success and is preparing this three-year-old start-up for its next round of funding by putting in place a reputable revenue process. Caroline is passionate about understanding the buyer and delivering products that are easy to buy, are easy to use and meet an urgent market need. She enjoys participating in all aspects of the sales process, including getting into the weeds and understanding each step of the buying process and training sales teams how to close deals and run sales calls, and she also likes to step back and set the strategic goals for the revenue teams. Before joining PowertoFly, Caroline worked at Bloomberg in a number of roles including head of sales for Bloomberg Government and head of sales training for Bloomberg BNA. Prior to Bloomberg, Caroline worked at CEB for eight years as a large-enterprise sales leader. She has her BA in English literature from Princeton and her MBA from Georgetown University. She lives in Washington, D.C. with her husband and two young children. Caroline, I’m so excited to be talking to you today. Why don’t you give us a little more information and fill in some of the blanks?

Caroline Turner: Well, Fred, thanks for having me. I certainly love talking about sales. One of my fundamental beliefs is that sales is definitely something you can learn. It’s not inherent with the personality. And so I’m really excited just to talk about ways we can really break down the sales process and help everybody be more effective at closing business.

Fred: Excellent. I’m excited to talk to you today about your sales history and how you got to all the success. And then we’re going to, throughout the conversation, get some tips from you for the sales game changers listening today. So tell us a little bit about what you sell today and what excites you about that.

Caroline: Oh, I’d love to. PowertoFly is a diversity talent platform. We help companies that are really serious about diversity reach and hire more women in fields where they’re underrepresented, and we usually help folks hire more women in tech and in sales. So it’s a really hot field right now. I think everybody is looking to hire more women to better represent their own marketplace, and PowertoFly help makes that connection happen.

Fred: The Institute for Excellence in Sales, our sponsor, has a Women in Sales program, and we’ll talk about some of that throughout the day. But how did you first get into sales as a career?

Caroline: So my first job out of school, I was a sales trader at Deutsche Bank, on the trading floor,. I had 30 institutional accounts and I was helping those folks trade equities in the international markets. It was a wonderful view of global companies, the global markets, and what I learned really fast is that the only way to differentiate yourself as a sales trader is to bring value to those clients. And so, very early on, if you’re not teaching the client something new they don’t see you as a trusted partner. You’re not going to win their business.

Fred: What were some of the key lessons you learned from some of your first few sales jobs?

Caroline: Before I went into sales my biggest, I guess, accomplishment was that I was an All American Lacrosse player, and I think in that role as well as in sales the most important thing is to get the fundamentals right. As any athlete has learned, you’ve got to throw and catch and do the basics, and sales is the same way. You’ve got to prep for calls effectively. You’ve got to ask good questions. You have to have the other person talking most of the time. You need to show a demonstration that aligns to what folks are looking for. You need to handle objections well. And so I think CEB really was wonderful at breaking down a sales process and understanding what to do through every step of the way, and once you have those fundamentals down, you can then morph it into your own specific sales style. But you have to get the fundamentals right.

Fred: So, obviously, when you’ve played a sport, you’ve had to practice, and that’s one of the themes that’s come through in the Sales Game Changers Podcast as well: Before you even get on the field you had to have practiced if not tens of thousands of hours, thousands of hours at least. And in sales, not everyone practices before they get in front of the customer… What are some of the things that you encourage people to do for that type of practice and preparation?

Caroline: One of the things I love to do when having a one-on-one with a sales rep and preparing for a call is to role-play how it’s going to go, and I say, “Walk me through what you’re going to say when this person gets on the phone.” Just to kind to start to practice hearing them say it. And then, as soon as they say it, you can either help to kind of tweak them a little bit and say, “Great. But also say this,” or you can just reinforce that they’re absolutely going in the right direction. I think that role-playing right in advance of a call is great. And, of course, the debrief. After every call I try to sit down with folks and say, “Tell me one thing you thought went well and one thing you’d do differently next time.” So it’s very positive and allows someone to do a little bit of self-diagnosis, and I give that same feedback, one thing I thought went well, one thing I’d do differently next time. And another thing I thought that CEB was really good at is that it was a constant feedback loop of after a call, really diving into “how can we continue to improve on our process?” and not taking it personally but [instead viewing it as] a constant evolution of our skill set.

Fred: Very good. So what are you an expert in? Tell us a little more about your specific area of expertise.

Caroline: I excel in understanding the buying process for C-suite executives in the Fortune 500 universe—so everything from getting into a company cold to landing and expanding with an account, understanding the buying process, understanding the procurement process and the legal process, and trying to be the best partner you can to these companies. What I found is that if these are organizations you’re going to be working with for your entire career, you want to make sure they’re buying the right thing for the right moment. And if it’s not the right fit for them right now, that’s okay because, again, it’s a long-term relationship you’re going to have with these folks.

Fred: What are the two biggest challenges that you face today as a sales guru?

Caroline: I think simplifying is one of the biggest. We have so much information at our fingertips now to share with clients. People can only absorb so much, so I constantly try to pair down our offering, our pitch to make sure it’s very pinpointed to “what is the market issue?” and then “how are we solving it?” So that’s one huge one: Just keep it simple—and of course, as a result, you make it easy for folks to buy. The other one, and I’m sure a lot of managers deal with this, is “Well, so I have a 100% remote team.” I had a remote team as well at CEB. I think you just have to work harder to make sure that the communication loop is constant, that everybody feels in the loop of how it’s changing in the marketplace, if there’s a new pricing option, if you’ve got a new product rolling out. You have to overcommunicate managing a remote sales team.

Fred: I want to go back to what PowertoFly’s mission is. You talked about getting women into technology jobs and sales jobs. What are some of the hindrances, do you think, for women in sales? What are some of the things that are maybe stopping them from being as successful as they could be?

Caroline: I think sales is such a great career for women. I think when I’ve talked to some very large enterprises where it gets difficult is when folks are midcareer and start having kids and travel is a requirement. That’s when women start to fall out of that role and choose to take a different path. Technology has really changed this. You know, the WebEx meeting screen-sharing platform has taken out some of the need to actually go in person. And then, some companies are really getting it right by making it easier for folks to travel if they have young children. I also think it’s really important to have key mentors and more sponsors throughout the way so that when you start having a family they understand… Otherwise, I’ve seen people quit jobs because the company’s not flexible enough to realize you’re at a place in your life where that’s not going to work. It doesn’t mean it won’t ever work. It’s just that right now it can’t.

Fred: I want to learn a little more about what PowertoFly does. What are some of the programs or some of the initiatives that you do to help women who have chosen sales as a career?

Caroline: At this point we are trying to put a spotlight on the companies that have made staying in sales as a career for women successful. For example, we did a podcast for sales a few weeks ago with Dell, and there were account executives across the United States, and we featured two senior women at Dell who’ve been there for 15-plus years. They talked about their best practices as women in sales at Dell but then also talked about how Dell allowed them to move for a relationship, to work from home when they had children, so a woman could see herself in that role and say, “Yeah, this is exactly what I’m looking for. I don’t have to sacrifice my personal goals to fulfill my professional goals.”

Fred: You know, when we created the IES Women in Sales program we had a number of focus groups to understand what they wanted. The four things that they said they wanted: build a community, a trusted community; second, build business development networks if you will; third, get better at sales, you know, become better professionals; and fourth, they were looking for a leadership track—you know, some advice from mentors on how to keep working more effectively as they grow their career. So I’m really interested in the mission behind PowertoFly, and our Women in Sales program has been absolutely phenomenal, and getting more and more women into professional selling has just been so rewarding. So I’m glad to see that’s the mission of PowertoFly. You’ve had a very, very successful career. Take us back to the number-one specific sales success or win from your career, Caroline, that you’re most proud of.

Caroline: It is a great question because I think in sales you could have so many wins and also so many losses along the way. But the one that stands out to me the most, it was 2008, post bust on Wall Street, and I think it was Q4. We were rounding out the year and if we didn’t hit our number there were going to have to be layoffs. I remember our business manager at that time coming to me and saying, “This is the number you have to hit. Otherwise we’re cutting.” And it was just so clear to me as a sales manager that there were jobs on the line. It was a very clear goal of how to stop that, and we had to get there. And so we got the team very focused on an outcome. We pushed and pushed and closed every day we could, and we hit that number, and our division didn’t get impacted. We didn’t have any staff cut. And I think that was the most powerful because we were still a new product that I knew resonated. Even in a downturn we were able to get folks to say yes, and all these hardworking folks didn’t have to lose their jobs.

Fred: You’ve been in sales management, and you’ve also been an independent sales consultant professional. Which do you like better? Did you like being on the road, being an independent individual contributor?  

Caroline: It’s interesting. I liked both. In a start-up, I’m actually doing both now, and what I’ve realized is that if you’re in a new company, if you haven’t actually carried a bag and sold, it’s really hard to relate to the salespeople and to really start to tweak the process very effectively. So I’ve been for about a year now actually selling and also managing the team, and I’m just kind of getting rid of my goal and my territory at this point. and I’ve enjoyed both very much. So I think for a period of time selling is wonderful, and then once you know the process, my favorite thing is to take a step back and teach it to everybody else.

Fred: Do you enjoy the mentoring side? Do you enjoy working with people you see something in who you think can be successful in a career in sales?

Caroline: Oh, I love it. I think, again, sales can absolutely be taught. I often compare it sometimes to the book Moneyball, where in the beginning there’s this whole philosophy how in the past you picked a pitcher by who’s tall and handsome; that was the right guy to pick. And I’ve seen that sometimes with folks who don’t understand that selling is not about personality, where they try to pick the person who’s got a big personality and is an extrovert, and that’s not what sales is about at all. Sales is about people who are good listeners, who have great attention to detail, who are not afraid to ask for money. And so, being able to help identify through behavioral-based interviews that people have those skill sets… very similar to The Challenger Sale, right? That they can teach, tailor, and take control and then nourish that in them. So, taking a lawyer and making them a great sales rep or taking somebody who was an account assistant or an executive assistant and seeing in them that they had great sales skills—that’s really rewarding because it’s hidden within them and we can help pull that out just by some training and direction.

Fred: In doing interviews for The Sales Game Changers Podcast there are a number of trends, obviously, that we keep hearing and keep saying. One of them is the nature of the customer has transformed, and you mentioned The Challenger Sale and that the customer has so much information at their disposal right now that they’re not necessarily looking for the sales professional as they might have 10, 15, 20 years ago to teach them and to educate them. So now, you need to truly bring real value. You really need to make a difference. You need to understand the customer’s business: not just how your solution can help but how you can help them with their daily challenges, and the customer has so many more challenges now.

So, anyway, you’ve had a great career in sales. Did you ever question being in sales? Caroline, was there ever a moment where you thought to yourself, “It’s just too hard, it’s just not for me”?

Caroline: I think getting my MBA was one of those moments where I pulled my head up from the sand to say, “What else is out there?” And I went right from college into sales and just put the pedal down. What I learned getting an MBA was that the sales skill set is unique and not everybody has it. Similar to being a finance person or a marketing person, having sales is really special and critical to an organization, and it was then that I realized that I had a unique skill set. I needed to own it and stay with it because it brought so much value to organizations, and in turn you can teach other people the sales skills. We’re not at the point yet, I think, universally where we’re teaching sales at universities or MBAs, and it should be a class because you are able to teach it, and folks would really get so much benefit from learning it.

Fred: PowertoFly has a very impressive mission helping women in their careers in technology and sales… I want to talk now to get some tips on how you can get better in your career in sales. Caroline, what’s the most important thing you want to get across to selling professionals to help them improve their career?

Caroline: There are so many things, but I think the most important thing is to understand your buyer. One of the things that I did when I first came into Bloomberg Government and I was running their federal contracting sales team was to bring in someone to walk us through. If you were trying to sell to the federal government, what does your day-to-day look like down to hour by hour, what do you have to do all day long. I think the more you can get your head into “This is what my objectives are, this is how I’m being measured, this is how I’m going to get my bonus paid out,” you’re so much more effective at asking good questions to aligning your product to their specific needs and to basically get into the yes of closing a deal. Having been on the other side of the sales process and buying when I was at Bloomberg, CEB’s sales leadership council was able to push it through internally because I was able to align that product to a specific business need because I understood internally exactly what the priorities were. So the more you can understand your buyer, the more you can position your product to meet that need.

Fred: Give us some of your ideas on how the people listening to today’s podcast, the Sales Game Changers, can better understand their buyer? What are some of the things they need to be doing to be at that level?

Caroline: What I’ve seen be really effective is in a sense very basic: attending as many calls or meetings in person as you can. When I went to Bloomberg Government, the now-president of that unit did not pick up a sales territory, but he made it a priority to attend at least five sales in-person meetings a week. And so he got very, very good at understanding the buyer so that he can be more effective at informing the people on his team about which way the product should go, different strategies for sales, different pricing ideas. It’s again getting as close to your buyer as possible by listening to those calls. I had been on the other side of that as a manager, where you get so high up and you’re managing spreadsheets and counting the number of first visits that you’re not at the ground level anymore, and you lose something. So I think it’s really important to get down as much as you can with the troops and hear what the buyers are saying.

Fred: So you’re a Sales Game Changer. You had a very, very successful career. Tell us some of the specific things that you do, Caroline, to sharpen your saw. What are some of the things that you do on a daily or weekly basis to stay fresh?

Caroline: One of the things that I really enjoy doing is being on those unhappy-client feedback calls. You’re going to have people who are unhappy with your product. They’re going to drop, and that feedback is so invaluable, when somebody is willing to take the time to tell you why they didn’t see value. I love being on those calls. It’s a gift. With that feedback, you get to a couple of things: We didn’t sell them the right product, we didn’t onboard them correctly, they’re not the right buyer. But all of those things help to inform both our go-to market strategy and the product.

Fred: Tell us something you’re working on today. What’s a major initiative you’re working on to ensure your continued success?

Caroline: Internally what I really want to put together is a comprehensive onboarding plan for new sales reps. I had run sales training when I was at Bloomberg BNA and we onboarded 30 new sales reps a year for a sales team of 150, and there’s such a risk when somebody new comes onboard. It’s a huge time sink for the manager. It’s a huge risk for that sales rep. And often, those folks don’t work out. You know, a third of them kind of wash out within their first year. And so, creating an onboarding plan that is approachable, that folks can do on their own but then also can do with a manager to keep them up and running faster. And a big part of it is understanding the buyer, being able to pitch the services, being able to objection-handle correctly, understanding the competition, that’s really important to me. I think it makes everybody more successful, and it then also makes the folks who are coming on feel very comfortable and invested in the organization.

Fred: Sales is hard. People don’t return your calls or your emails. The customer has changed. Why have you continued? What is it about sales as a career that keeps you going?

Caroline: It’s two things. One is I enjoy the problem solving. I think it’s so intellectually stimulating. To get on the phone with someone and to hear what their challenge is, why they took your call, and can you solve or help solve their problem with your product. I really enjoy just the mental gymnastics you have to do in a call, when you’re doing that dance of what can we do to support you and how can I present this to meet your need. The second one is that if you believe in your product, they’re all going to buy eventually, and I do believe that… So you’re starting the conversation now, and as the product evolves and you understand the market more, you’ll find that product that’s going to fit their needs or the buyer from whom this is the great fit.

Fred: You know, I’m going to ask you one more question before we wrap up here today about the company you work for, PowertoFly. I can hear the passion that you have for the mission. Just give us a couple of sentences about why you’re so passionate about the mission behind PowertoFly.

Caroline: When I was a lacrosse player, my father would come to all my lacrosse games with a Title 9 hat. It was very much like women should be doing everything that men do and there should be equal opportunity for all. And I think that’s what I love about PowertoFly. It’s helping to keep women in the workplace and not fall out when their lives get more complicated. I have two small girls. I get how hard it is to do the balance, and PowertoFly is basically making that conversation. I’ve seen having that conversation loud and clear with corporate America. We’re not hiding it anymore, where you don’t have to pretend that you don’t have kids at home. It’s okay if you have kids at home and you need to leave at five o’clock. It doesn’t mean your productivity is going to go down again. Working for companies that get that and are making it possible for women to balance it all or integrate it all makes a huge difference to me, and it gives me just a real reason to fight every day at PowertoFly.

Fred: The website is PowertoFly.com, so check it out.This is the Sales Game Changers Podcast. My name is Fred. We have been talking today to Caroline. Caroline is the chief revenue officer, the CRO, at PowertoFly. She’s given us some great insights on how you need to bring value to your customer, how you need to be preparing yourself to understand the challenges that your customer is going through. She talked about some strategies for women in sales to be more effective, talked about the need to simplify. She also gave us some analogies from her lacrosse-playing days at Princeton and how that has served her as a successful sales game changer. Caroline, give us one final thought to share with the sales game changers listening today to inspire them.

Caroline: I think the thing that has been most effective for me is to find that product that inspires you—something you feel passionate about that will come out in your voice every day. I’ve sold products that I believed in, hand over heart, and others that I believed in the company but that specific thing didn’t get me up and excited every morning, and it makes a huge difference. There are a lot of things you can sell in your career. So find that thing that you’re excited about, whether that’s golf carts or compliance best practices. Find that thing that you love and just go with that. It will all pay off in the end because people will hear that passion in your voice and they’ll believe in you as well.

Fred: I agree. So again, this is The Sales Game Changers Podcast. Thank you so much to Caroline for being on today’s Sales Game Changers podcast episode. Caroline, how can our audience reach you?

Caroline: I’d love to hear from folks. My email address is Caroline@powertofly.com.

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