EPISODE 445: Salesforce Sales Leader and Blue Angels Pilot Katie Cook Says Women in Sales Must Have this Mindset for Career Success

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[EDITOR’S NOTE: This is a replay of the Women in Sales virtual learning session sponsored by the Institute for Excellence in Sales on December 1. 2021. It featured an interview with Salesforce sales strategy leader Katie Cook.]

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KATIE’S TIP: “I use the same phrase when people ask me, “I want to be a Blue Angel someday. How do I get there?” I say, “Calm seas don’t make a skilled sailor.” What I mean by that is it’s not the easy times in your life, it’s not the calm seas that shape you as a person. It is those hard times. It’s the rough seas. It’s the failures. It’s the adversity that you face. How you deal with that, that will shape you as a person, as a mother, as a spouse, in my case, a Marine, a leader, and now as a businesswoman. That’s really what I would say, is adversity is a way to improve yourself. Rather than get down in the dumps about it, use it to polish yourself.”


Gina Stracuzzi: I’m very excited to welcome Katie Cook from Salesforce to the program. Katie went through the forum, and I loved watching the transformation. It was really quite something. Welcome, Katie.

Katie Cook: Thank you so much for having me. It’s great to see you again, Gina.

Gina Stracuzzi: Great to see you. Katie, with the Fresh Voices we usually start off with, where did you go to school? What was your area of study? Did you think you were going to end up in sales? Your trajectory to this point is remarkably different than most people. Why don’t you start at whatever point in your life you want to and tell us all about it?

Katie Cook: I grew up as a Navy brat. My dad did 26 years in the Navy. I moved all around the world, including went to high school in Japan and all this. Moved around a lot, got to see a lot of amazing things, and learned how to make friends every two years, if that makes sense, and make connections with people in a very short timeframe. I followed in his footsteps and ended up going to the United States Naval Academy where I studied political science, so not a business school. I studied political science and then I went on to Georgetown and got a master’s in international security. I then commissioned as a United States Marine, I did 12 years active duty as a Marine. I was a C-130 pilot, which is a very large aircraft, four prop engines. I did two deployments, one to Afghanistan, and then one to South Sudan, where we evacuated the embassy in 2014.

Then I actually got selected to fly for The Blue Angels. For those of you that are familiar, I was the first woman pilot ever, and have been since, to fly for that team. It was a really great opportunity to show little girls and even little boys that you could grow up, and even if there hasn’t been someone that maybe looks like you, has a different race, or gender, or sexual orientation, maybe upbringing, you can still carve your own path and you can still achieve your dreams. That was a really great opportunity to do that on The Blues.

Then I ended up having two children and my priorities changed, and I decided that active duty Marine Corps wasn’t for me anymore in the cards. I transitioned to the reserves and that’s when I started looking for my next mountain to climb, I guess you would say. I luckily ended up at this amazing company, Salesforce. I was originally hired as a project manager because I went and got my PMP when I was transitioning out of active duty. I was brought on to do a project, our five-year business plan, how we were going to grow the public sector abroad for Salesforce. Through that I got into a lot of strategic decisions and strategic analysis for the growth of the business.

I ended up moving over to sales strategy and I have now been with the company for two years. I’m a Director of Sales Strategy working directly for COO in public sector and I absolutely love it. I have two really awesome women who work for me as well. It’s awesome to pay it forward from the lessons that I learned in the Women in Sales Leadership Forum to the ladies who work for me now and being able to pass on some of those things. It’s been a wild ride, if you will, and definitely not traditional.

Gina Stracuzzi: Definitely not. There’s so much to unpack there. Before we get into the flying, and I’m staggered by the notion that you are the first and so far the last woman to fly, which says a great deal about you, but not so much maybe about the organization. But that’s a beast we can beat some other time. Tell us a little bit about international security and that education, what you use of it in your career today in terms of strategy. That’s just really interesting because I’ve known a lot of people that have studied international business, and international diplomacy, and international studies, and security is another topic altogether. How have you used those two together in your sales career?

Katie Cook: I would say one thing that international security, my degree, has helped me look at things from a strategic level. The Marine Corps does the same thing where we look at things from a tactical, operational, and strategic level. In my job currently, I’m not necessarily in the trenches carving territories, like some of our sales strategists do. Instead, I’m helping our key leaders figure out where they want to take the business. What new markets are we going into? Where are we going to place headcount investment? What other security investment do we need to make to be able to do, say, data residency or compliance with local laws as we’re going into these new markets, specifically in EMEA and the APAC areas? I think that has helped me, my previous degree has helped me look at things from a strategic view, rather than the tactical view.

I would also say that I think it keys me into a little bit more how our security posture can affect business. The pandemic is a prime example. Salesforce, particularly public sector had an enormous year last year because we were involved in contact tracing, vaccine dissemination, and they were helping solve this security problem, which is, as much as people don’t look at it that way, the pandemic is a security problem. The same thing can be said for our global security position. For example, if China attacks Taiwan, that could be something that very much impacts Salesforce business as well as business at large. If Russia attacks the Ukraine, again, that could definitely impact our business in EMEA. I think that’s the stuff that I look at a little bit differently than probably the average person, of how our global events maybe in the defense sector or the military side of the house could have impacts long-term on the business.

Gina Stracuzzi: I know within your organization, Rita DeFilippo, she is so eager to bring women coming out of the service into sales because she can see how there’s a direct correlation between that strategic thinking. Then also knowing risks as they apply to global environment, which we’re working in now. We had a fantastic conversation about it several months ago, and it made a lot of sense to me. It really made a lot of sense. I think recruiters might want to start setting up shop on base and in those exit programs, because it could really go a long way to making that bridge make more sense and go a little smoother, because you know that transition out of the military life can be quite hard. My husband went through it too, and it’s difficult. Having a path really makes sense.

Katie Cook: Salesforce is wonderful with that. We have Salesforce Military, which allows transitioning vets and their families to get free Salesforce training where they can go on and get hired as Salesforce admins and get into the Salesforce ecosphere and have all of that support. We focus on hiring veterans and those intangible skills and we’ve actually established a military recruiter now this year, Mike Nolan, at Salesforce, who specifically looks for military veterans and helps get them positions at Salesforce that work for them and their skills.

Gina Stracuzzi: Rita and I were specifically talking about the transferable skills into sales too, which made a lot of sense. Really because people feel like they either have to come in at the beginning of their career, or they can only change from another company doing sales. But it’s really mid-career where people have some training and they have some good people skills and they really cut their teeth maybe on a different industry, but they bring invaluable knowledge. I know companies are really struggling to find good salespeople, so that might be a great place to look.

Katie Cook: For sure. I think Rob Stein, who’s also very much involved with the Women in Sales Leadership group, he very much pushes that idea of, “Yes, we are in pub sec, but we don’t necessarily have to be grown in pub sec to be great salesman.” He also really is invested in veterans and suicide prevention in veterans. It’s really great to have advocates like that in the public sector at Salesforce.

Gina Stracuzzi: Absolutely. Usually at this point, I ask my guests about their first leadership role. That’s a really broad question for you, I’m sure you can pick quite a few things. What do you classify as your first leadership role and how did that affect you moving forward?

Katie Cook: In the Marine Corps, obviously you are a leader from the very beginning. Especially as an officer, they put you in either peer leadership positions or informal leadership positions. I would say I was a commander of 130-person company where we ran a small airfield in Eastern North Carolina. This airfield was expeditionary, meaning it’s not made out of a paved runway that you see. It’s made out of AM2 or aluminum matting. It’s very, very unique and it can be laid down and picked up in 72 hours. That’s why we call it expeditionary. You can literally build an airport in 72 hours, which is amazing.

I ran this airfield. I was the person with 130 other amazing Marines. I would say that was my first formal leadership of a large group of people. I had one or two people before, but that was my first time doing that. I would say it was really unique because, one, I was a pilot and I was now leading firefighters, I was leading the airfield maintenance people, fuelers, and airfield operations people. I had a lot of people who were subject matter experts of things that I had no knowledge in. I had to learn how to trust and delegate and really learn. I felt like my knowledge was a mile wide but an inch thick. I couldn’t dig into all of the things that were specific about fuels, but I knew enough to make smart, safe decisions and be advised by my subject matter experts. I would say that was my first experience at formal leadership position.

Gina Stracuzzi: I would think it would set you up to handle just about anything. It makes me think about so many stories that I have heard doing both the podcast and through the forum, where it’s 50 men in a room and one woman. Did you find a lot of pushback on your leadership as a woman in a pretty male-dominated environment, and how did you handle it?

Katie Cook: I would say from my subordinates, or those that I was leading, I got very little pushback. They knew that I was an authentic leader. They knew what my expectations were. If they didn’t meet those expectations, there would be consequences. If they met those expectations, then I was their biggest champion and I was going to push them for whatever opportunity they wanted, whether that was awards or promotions, or whatever. I was very straightforward and fair. I never had any pushback from those that I was leading.

I would say the biggest pushback I got was probably from my peers, in that I was really, really good at my job. When I outshine you, it’s always attributed to, “Well, it’s because she’s a girl and they need a woman. There’s a quota to fill. She’s getting extra opportunity.”

Gina Stracuzzi: Yeah, they got to check that list.

Katie Cook: Right. A lot of times they just couldn’t grasp that I was better than them. I don’t mean that in a very callous or pompous way, it’s just the truth. I was a very good pilot. I spent time and I worked hard for my Marines. I think that was the biggest pushback, was from my peers.

Gina Stracuzzi: I truly applaud you for speaking that truth, that you were just damn good. Because a lot of times as women, we go, “Yeah, well, I did okay.” The truth is, when we’re good, we’re good, just like guys. There’s nothing to hide behind and there’s nothing that makes people more nervous than someone who is really good and takes their job very seriously, because that’s a threat. That can be applied to current situations too. How did you get to Salesforce?

Katie Cook: It’s going to sound funny, but my husband and I, because he was also an active duty Marine, Blue Angel like me, who now also works for Salesforce, so we’re a Salesforce family. But we actually just pulled the top companies to work for in the country. We pulled that list and then we went through and said, “What companies align with our values?” Because the Marine Corps is not just a job. It’s a culture, it’s a lifestyle. Instilling these ideas of honor, courage, commitment, and this life of service that I had done for 12 years, I couldn’t just give that up. I still wanted to be in a company that had those values of serving their community, of giving back, of even support DOD.

I ended up looking at Salesforce, as it’s one of the top companies to work over the past 10 years. I was actually supposed to do a talk with them, because I have a small business on the side where I do public speaking, and I was supposed to do a talk, but I ended up getting pregnant, couldn’t travel. I reached back out to that point of contact I had and said, “Hey, I’m transitioning out of the Marine Corps. Do you think there could be a spot for me?” My resume ended up in front of Keith Block, who was our co-CEO at the time. Then it got passed down to Lisa Edwards, who was on our ELT at the time.

Then it kind of trickled down to pub sec, where Kevin Paschuck, who’s our current EVP CEO in charge of public sector EMEA, took a chance on somebody who did not have any business experience at all. But from recommendations of my current boss, like Russ Craig and Rita DeFilippo, that you mentioned, ultimately took the chance on me and saw those intangible skills that came with somebody who had 12 years of military experience. I would say, knock on wood, it’s starting out for the best. I’ve been here now two years.

Gina Stracuzzi: That’s wonderful. What about your husband? What’s he doing in Salesforce?

Katie Cook: Dusty is much more I would say nerdy than I am, in a very loving way. He’s very technically savvy when it comes to computers. Even though he was a C-130 pilot just like me, he was a political scientist just like me, he did get his MBA, PMP, we walked very similar paths. But he worked for Red Hat, a small tech company out of Raleigh. He worked for Red Hat for a couple of years and then is now a solution engineer. He is going to be those that are developing those demos and showing the customers what to expect. If I had to be a betting woman, I would bet that he’s not going to be a solution engineer his whole career. I could see him falling in love with sales. We’ll see.

Gina Stracuzzi: Right now he’s coming up with things and you’re selling what he’s building, basically [laughs]. What are some of the most vital lessons that you’ve learned along the way? Especially, talk a little bit about what you’ve learned as you’ve transitioned, because there is an ease about you now that I didn’t even see six, nine months ago, when you started the forum. You were still very military, and you were yes, ma’aming me, which was very sweet, but always makes me feel very old, but I knew where it was coming from. But that seems to have melted away, so tell us about that.

Katie Cook: I would say, when I was going through the forum previously, I had just come back from baby leave. Those of you that don’t know, the day I got my offer letter from Salesforce was the day I found out I was pregnant with my third child. Imagine that day. I did nine months at Salesforce working for Rita DeFilippo, which was amazing. She’s an amazing boss. But at the time, I was under water. I was trying to learn everything I could about being in the civilian sector, being in business, learning about Salesforce. I was just trying to claw my way through it. Then I left for six months for my maternity leave. When I came back is when I was right in the forum with you, is when I started.

I would say my transition to the civilian sector didn’t really occur until I came back. I went through the forum and I learned a lot of these lessons from all of your amazing speakers and the other women who were in the forum with me. I’ve continued my mentorship lessons with Rita and my current boss, Russ Craig, who when I came back from maternity leave, I transitioned from Rita to Russ’s team, has been an amazing mentor to me. He has three daughters, and so I think he sees me as his bonus daughter, and has really brought insight into the corporate structure, the politics that come with that, that I was kind of unaware of.

Even to this day, with Rita, for example, I was really, really annoyed at someone in my company because they were going outside their job description. They were doing a whole bunch of other stuff. I was like, “Why don’t they just stay in their lane?” Rita’s like, “That’s a very militaristic way to think of it.” For us it’s the firefighter does firefighting stuff. The fueler does fueler stuff. To me, I was still thinking very much in that mindset, while she’s like, “The corporate structure is that you need to grow outside your role to even look like you’re going to be promoted.” There’s still things that I’m struggling with in the transition, but finding amazing mentors that I think are not military veterans has been to my benefit, because they can see where the disconnect is between my perception and theirs, and then bridge that gap. That’s definitely what’s helped me for sure.

Gina Stracuzzi: Well, Tamara Greenspan, who spoke to the group about the importance of mentors and sponsors, will be happy to hear that. What would you like to share with others, especially those that might have an unconventional path into sales and sales leadership? What advice do you have for them?

Katie Cook: I would say imposter syndrome is real. Imposter syndrome is so real, and I have experienced it I would say tenfold over what I experienced in the Marine Corps. I think about my time on The Blue Angels. I showed up there, and you can ask my husband because he was on the team with me, that I was nervous as hell for my first show. I knew that I could fly really, really well, just as well as the men who had been on the team before me. I knew I was there for the right reasons. I knew I wasn’t selected just as a quota, but I deserved to be there. I still was so nervous to mess it up that I had the weight of the world in my shoulders. “If I screw this up, then no woman is ever going to be selected for this team ever again,” is kind of how I felt. I felt like people were hoping that I failed.

I came to Salesforce, and even though I have so much confidence in my ability as a Marine, I kept telling myself like, “You don’t know what you’re doing. You don’t have any business acumen. You don’t have your MBA. You have a political science degree. You have no idea…” I was telling myself this stuff every day. I was my own worst critic, my own worst enemy at that point. I really think it took my husband and people around me, and I’m not usually one of those that needs a pat on the back, that’s not the lifestyle you go into in the Marine Corps if that’s what you need all the time. But having people like Rita, like Russ, like my husband, give me honest and real feedback of like, “You are doing good. You are filling a gap that we never had filled before and we are this much more productive.”

Now that I’m in sales strategy and a very numbers-based person, I can see how my impact is having a direct impact on sales, or the efficiency of our leaders, or just being able to support our COO to work more efficiently. It’s being able to tell myself that, “I deserve to be here. I have these intangible skills.” I think to wrap all of this up is that imposter syndrome, you would never tell another woman the things that you tell yourself. I would never tell another woman they don’t deserve to be there. We should be giving ourselves the same grace and the same support that we give other women. It took handholding from Rita, and Russ, and my husband to get me there. Now I think I’m a lot more confident in what I’m doing and I know that I deserve to be here and that my opinion matters and I give really sound judgment. If Dave Rey trusts me, then I need to trust myself.

Gina Stracuzzi: That’s great advice for others too. You know it’s something we drum home in the forum too, that we need to get out of our heads and just let our knowledge, and our experience, and our confidence, albeit the small voice, take the lead. Because we know what to do, we just need to get out of our own way. That is really great advice. Let’s talk a little bit about sales leadership and where you would like to go with your career from this point.

Katie Cook: I’m currently, like I’ve mentioned before, working directly for our COO. I’m getting a lot of great operations experience. I like the operations area, or the capability where we identify shortfalls, we identify white space, we identify trends, we identify problems, and then come up with solutions to fix them to enhance the capability of our amazing AEs and sales leaders. I think I would like to stay with an operations background. However, I think I would like to move into more of a chief of staff role and more formal kind of leadership decision making ability role eventually.

I know that I only have two years under my belt in operations, and so it may be a little bit longer to build up that experience. I have an amazing mentor in Russ Craig, who’s increasing my knowledge in that. Of course, Dave Rey, who sets an amazing example for leadership, particularly in sales, and is a great women’s advocate. I have these really amazing examples to learn from right now, but I hope throughout my trajectory, is I think my skills as being an air traffic controller, so to speak, in the organization, where I connect people. Maybe I don’t have the answer, but I can find the person who does, I have those great relationships throughout the organization. I’m extremely organized, I’m really detailed oriented and all of these things that I’ve learned from the Marine Corps, and emotional intelligence, all of that, I think would serve me really, really well in a chief of staff role. I think that’s ultimately where I’d like to grow too in the future.

Gina Stracuzzi: Chief of staff, it’s kind of a new thinking for a lot of corporations. It’s big in the military and it’s just a new lexicon, if you will. They’ve had those people who are almost like the confidants and the people that they can trust to make decisions on their behalf and write things for them or whatever, but they’re just not called chief of staff. They have a myriad names. But I get where you’re going and I’m sure that you will get there as corporations especially start to change their thinking a little bit.

Katie Cook: Salesforce is that way. There are more chiefs of staff coming on. I believe Ebony was named the chief of staff of the ELT. There are more and more chiefs of staff being populated more at the higher levels of Salesforce. I truly believe as it trickles down from the ELT level to our OU level, and maybe even beyond, that chiefs of staff could be force multipliers. Right now we have COOs who are working 80-hour days, when if they had a chief of staff could handle some of that small stuff, could handle the slide building and the speech writing or whatever you need to do, while they handle the more strategic view. I think we could be more efficient in that way.

Gina Stracuzzi: You’re probably going to have all these offer letters coming through now. Salesforce is going to have to place security locks on you to hang onto you. But you’re clearly very happy there and they know the value that they have in you. I love seeing that. Nothing’s more depressing than seeing good talent wasted because people don’t have the vision. We are pretty much out of time, but do you have one piece of parting advice that you would give the listeners that they can put to work today in their careers? Especially if they’re looking to make a change or they’re thinking about going off in a non-traditional direction, anything of that nature?

Katie Cook: Actually, I use the same phrase when people ask me like, “I want to be a Blue Angel someday. How do I get there?” I say, “Calm seas don’t make a skilled sailor.” What I mean by that is it’s not the easy times in your life, it’s not the calm seas that shape you as a person. It is those hard times. It’s the rough seas. It’s the failures. It’s the adversity that you face. How you deal with that, that will shape you as a person, as a mother, as a spouse, in my case, a Marine, a leader, and now as a businesswoman. That’s really what I would say, is adversity is a way to improve yourself. Rather than get down in the dumps about it, use it to polish yourself.

Transcribed by Mariana Badillo

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