The Sales Hacker Podcast
The Sales Hacker Podcast

Episode · 3 years ago

62. How to Create, Manage and Incentivize Teams w/ Kathleen Roberge

ABOUT THIS EPISODE

This week on the Sales Hacker podcast, we speak with Kathleen Roberge, Chief Revenue Officer (CRO) at Rocketrip. She’s great at managing people and incentivizing teams. She’s so good, she gets results! She’ll also share her secrets on how to be a rockstar CRO.

One, two, one, three, three. Hey everybody, it's Sam Jacobs, your friendly neighborhood saleshacker podcast host. Welcome to the show. We've got a fantastic show. We've got Kathleen Robert. She's the chief of an officer at rocket trip sheet. The last I think three companies, maybe four companies that she's been at have all been acquired or ipoed. I think maybe it's acquired, but the point is she has an incredible track record, she's an incredible leader and she has a number of great insights both about how to manage people and how to incentivize teams, but also how to be a great chief for Revenue Officer. So I think it's I think it's a great interview. Now, before we dive in, we want to thank our sponsors, as we always want to thank our sponsors. The first one is Congo. CONGA is the leading end to end digital document transformation suite. With Congo you can simplify documents, automate contracts and execute each signature so you can focus on accelerating sales cycles and closing business faster. Go to gocomacom forward, slash saleshacker for more information. You know who our second sponsor is? Our second sponsor is outreach. That's the leading sales engagement platform. Dumb Dum. Outreach support sales reps by enabling them to humanize their communications at scale, from automating the soul sucking manual work that eats up selling time to providing action oriented tips on what communications are working best. Outreach has your back. Max Mark and many have also written a great book called sale engagement. If you haven't picked it up yet, it's on Amazon or anyway, you anywhere you can find great business books, and it'll teach you all about how to effectively drive pipeline, build pipeline and drive and drive engagement with your sellers and with your prospects. So it's a fantastic book. And then, finally, I want to thank our fans because we got a lot of people reaching out to us. We're hitting all time highs, so it's pretty exciting. The following people should be thanked and and complimented. In the PLOTT at Tanique Lenderman, thank you for reaching out. Mike Adams, Kyle Rudder, many Pardo, amy love at Philip Newcomb's summer ostler. That's a great name. Dan Hickson, Scott Colesworthy, Ryan Cullen and Brina Martin's. Thank you so much for reaching out for listening. If you're out there and you want to get in touch with me, please do so linkedincom forward in form F Jacobs. But for now let us listen to Kathleen Roberts, the chief revenue officer of rocket trip. Hey, everybody, it's Sam Jacobs. Welcome back to the sales hacker podcast. We are so excited today to have Kathleen Roberts on the show. Kathleen is a new chief revenue officer, or the new chief for revenue officer at rocket trip, but she is a career cro and sales leader. Let me just quickly tell you about her background. She spent twenty years growing technology companies through her focus on delivering strong go to market strategies, building demangin engines, opening new channels of revenue and developing customer success in Account Management Programs. Before rocket trips, she spent five years at a ventry where she was the crow, leading a global sales and account management organization and resulting in an increase in revenue by nearly six hundred percent. Before eventry, Kathleen was the chief Business Development Officer at Compuchhare, helping take the company to a successful acquisition through her strong leadership of sales and marketing. Earlier in her career, she serves as evp of sales and marketing at perimeter, one of the largest startup success stories in Connecticut. She graduated from Fairfield University and she contributes regularly to thought leadership, participating in twenty to thirty speaking engagements annually and publishing lots and lots of articles. Kathleen, welcome to the show. Thank you, Sam. It's great to be here. We are excited to have you and you know you've written so much to the point of the bio on sale. So we're really excited to dive in. But before we do that we like to take a minute and understand what we call your baseball card. So first of all, that I pronounce your last name correctly. You did, you got it, you got it right. Good and confirming. You are not related to mark Robertsh no, I wish I was, and you are the Curo at rocket trip. So tell us what rocket trip is. Sure, yeah, it's a...

...great concept. Rocket trip is actually a rewards platform in scenting travelers to spend less on travel. And so essentially what we do is we present each traveler with a price to be if they go below that price, they keep half the savings and the company keeps out the savings. So it's a win win for everyone. That is that is a great idea and probably takes the sting off of flying economy across country sometimes. Yep, absolutely. So, how big is rocket trip? Can you give us like a rough rur revenue range? Sir, we're relatively small company, less than ten million in revenue and we actually went through our most recent funding round was almost a year ago, and that was a fifteen million dollar series c round and it was led by Google ventures. Awesome, pretty, pretty exciting, because Google ventures is google. is where we came up with the concept for rocket trip. Oh yeah, I don't know that. Yep, Yep, Google travels program is very similar to the rocket trip concept. Oh well, how big is your team at rocket trip? And so and you're responsible at my correct sales account management. You run marketing. To tell us about your responsibilities. I have sales and marketing. I actually don't have account management. So sales organization is made up of SDRs and a's and we also have a business development team. Let's focused on partnerships, and then I have a marketing team which represents about five or six people. So it's about it's about twenty to twenty five people in the team. Wow, that's that's fantastic. And so you've been doing this for a while, since two thousand at might correct that. Are you in a on a streak where each company that you've worked for has had some kind of exit? Is that accurate? That is correct. Yep, I'm on a roll and I'm hoping it doesn't stop here. So you know, what were you saying? I was going to say. Yeah, so I started my career the first startup that I ever went to work for was this company in Connecticut called perimeter, and then it was a hosted security solution. I was actually there for much longer than I ever thought, but I was the third or fourth employee there. So that was a really, really true startup. But we sold that company and then I left and went to another startup, come to share, which is a west coast face company, also is a hosted solution. We were a man of service company and we changed it into a SASS model and I was with them for four years and we sold that company. And then more recently I was with a company called a ventry and that was through the end of two thousand and eighteen and again we had a an acquisition by a private equi firm and I'm now with rocket trip about six months. So wow, successful continue. Yeah, exactly. Rocket trip will be acquired shortly, if if the past is any indication of the future. So when you started a perimeter many years ago, was it as a cond executive? You know, was that your first job out of school? Walk? How did you get into sales? It wasn't my first job. Actually, I've been in sales my entire life. Funny Story is that I actually started in elementary school. I was always the the leader of the girl scout cookie sales. I actually used to have my parents buy boxes of candy at Costco and I would sell them in my middle school profit on. But I love sales. I love solving customers problems. Before perimeter I was very fortunate. I joined next help, I sure you remember them, the walkie talkies, them as an account executive and they gave me an opportunity to build out a new division of the company in the Northeast and I happily jumped on it, but I had no experience. I was just willing to give it a shot and that's where I learned a lot. I unfortunately had lots of failures, but I had lots of on the job learning. So after that I knew I really wanted to work for startups and I fell in love with perimeter, which was the first startup I work for right after next hell, and ever since then I've really been seeking sort of risky ventures with younger companies...

...that are solving real problems and they really just need help with the execution. What is it about the early stage companies that gets you so fired up so passionate? Yeah, I think, as you know, there's there's no bureaucracy. That's really about wanting to do the get the job done and doing it and and inspiring your team to do the same. So I love that aspect. I also love that smaller companies you can really make an impact and you can notice that you're making an impact, whereas you get lost in larger companies. So that's mainly been been my inspiration for starting going to start ups and when you think about sort of like leadership lessons, because you've been running teams now for quite a while. When you think about sort of like your first principles or how you approach a new situation. For example, you inherited a team at rocket trip. What are some of like the pillars of your management philosophy, your leadership philosophy and maybe even your sales philosophy? Yeah, sure so. I think one thing is what I call rapid experimentation, and this is, you know, taking risks and trying some new things that the company's never done before. And I always say that, you know, the risk of not experimenting is is greater than the risk of failure, and these don't have to be big disruptive risks or ideas. It's more about making smaller improvements and testing the assumptions very quickly. That's something that I really depend on when I'm when I'm in a small organization. Another another philosophy is don't be afraid to do crazy shit, trying new things, think out of the box. You know, really I I've done some things like, you know, I make people earn their spots on my sales team. You know, give them give them temporary positions and give them a set a list of criteria that they have to earn before I make them full time employees. I've done some really crazy things with distributed work environments and not being so fixated on having everyone in the office and even though that's typically the mentality of startups. Well, tell tell us more about that. I want to know about that. So what is the crazy thing you've done? You've it's been a distributed sales team or it's been a distributed inside sales team. Tell us what you did. Yeah, both. I think one of the craziest things I did was hired people overseas and they were employees. But this was a very small start up. It was probably two million dollar at the time that I got there. And we we've identified some some European candidates who were willing to work our hours and do a lot of inside sales functionality for us and they've proved to be wildly successful. So that is crazy. That is crazy. Yeah, so I think. I think you know, never limit yourself and always be thinking of, you know, what works best for the company, even if it's not the traditional or conventional way to do things. You mentioned rapid experimentation. Give us some examples there, because that that's always super interesting. Like what are some small, marginal, incremental improvements you've been testing over the last couple of years that that represent that idea? Yeah, I think. I think one good example recently that came up was pricing. I came into my previous company and there was a pricing model that was the standard, standard pricing model. You know, it's a subscribe, subscription, annual payment, and we had we were not a proven company and we had lots of people that said, how do I know that I'm going to get the return that you say I am? And I think sometimes when you're young, you have the flexibility to say things like well, let us put our money where our mouth is and let's do some things like pay in arrears. Let us show you that you can use the profits that you gain or the return that you gain from the solution and actually pay for the for the program and so things like that. I think it's really important to be flexible and to do innovative things and not be so stuck on the traditional, in this case pricing methodology. Seems to me that that sounds great in practice, but you also must be you must have some strategies for convincing your CEO or your executive team that these are not break the bank decisions. Do you do have a way of persuading people,...

...or do you have a framework for making this argument when you're in the exact meeting and you're saying we're going to we're moving off of up front payment, which everybody tells us we're supposed to do? Yeah, I think you know, I'm a pretty transparent person and when I start with a company I have a very frank conversation with the CEO and and sometimes even the board to let them know that I am going to experiment and that's what I was brought in to do, and so I try to get their buy and even before I come on board, that you know I'm going to be asking for some you know, their commitment and they're buying on some non traditional things and I think that's a you know, if they have confidence in you and they are willing to let you take some experiments, you know that up front and frankly, if they said no, we're not going to let you experiment, I would know that this would wouldn't be the environment that I would thrive in. So it's good to have that conversation early and up front make sense and I love it. I love it. I firmly believe in negotiating as much as you can beforehand so there are a few surprises as possible. One of the things that you said is team's over idea. Tell us what you mean by that concept. Yeah, I think. I think sometimes people think, especially with startups, that you know, it's all about the idea and how great the idea is. But one concept that I I always found is you could have the best idea ever, but if you have a team that can't execute, what good does it do you? So it's it's always better, I think, to have a great team than a great idea, and they'll figure out a way to execute and and and a way to even come up with a better idea if they need but it's really more about the people that you hire and the actual idea itself. What do you think the mechanisms are for building a great team, like? What are the strategies that you use to make a team great in the first place? Yeah, I think the whole idea about finding ways to motivate your team, and for everyone it's different. So I think investing time in your team and figuring out what is the one thing that gets them really excited is it? Is it money? Is it recognition? And once you determine that, I think you start to to play with those levers and really incentivize people based on what they're motivated to do, and so I had a lot of fun with that. It actually is goes hand in hand with the whole rocket trip thing, sentivizing behavior to do things that people wouldn't normally do but they would if you've sent them in the right ways interesting. So what are what are some example at? I guess one question I have is, you know, there's a lot of conversation and discussion that sales people need to be explicitly motivated by money. So have you found that? And I mean clearly it seems like you you may have a different point of view, but is that a problem if people aren't particularly motivated by money and sales and what are the other mechanisms? What are the other incentives that you use to drive behavior? Yeah, I mean I I wouldn't say it's a problem, but I've I rarely find sales people who aren't motivated by money. So they're pretty pretty easy creatures to motivate. And what I found is a lot of it comes down to the compensation plan and if there's a lot of upside in the plan, people work really hard to get to that upside. So I, you know, do my best to come up with plans that are probably a little bit over the top, but only if the person is successful. So it really gives people motivation to be successful. And the other thing I think too, is I think people sometimes get really caught up with monthly quotas and quarterly quotas and and you need to have those because those are good measurements throughout the year. But the thing that I typically find a lot more success in is if you if you develop compensation plans where the accelerators are based on the annual plan, so that people, very early on in the year, are striving to get to that number, that annual number, and are doing it as early and as quickly as possible because they want to get to those accelerators. So it's a it's a nice win win for both the salesperson as well as the company. So walk us through. So in a typical Complan, are your accelerators? One question I always have for a debate. I always have with the CFO is, are they paid on incremental...

...dollars or back to dollar one? You ever have comp plans where the accelerator kicks in and it goes all the way back to the first dollar soul? No, typically, typically not. It's typically once they reach a certain threshold. Everything beyond that is is accelerated, but typically doesn't go backwards. What's the highest payout for sentence you've ever built into accomplant? Oh Gosh, um. Well, I think it's interesting because I've done so many different things with complans. But one of the things that I found was really interesting, and the numbers can get very high, is when I was at Compu share, we were super motivated to get people who do long term contracts, and so one of the things I built into the plan was let's pay them on TCV, not ACV, and this lay will definitely be motivated. And so those those numbers can get high if you do pay on TCV. But we fixed our problem pretty quickly and people we had a lot of long term contracts. Interesting. Yeah, I mean t paying on TCV. That will there you go. That's an example of something that's controversial because the problem will exactly to your point. I mean unless you have really, really good like a deal desk or some kind of policy framework to make sure that people aren't jamming a massive basically using the TCV framework to give massive discounts on a per annual basis, because the end of the day, businesses are measured on annual revenue versus versus things like TCF r bookings. Was that a problem that you encountered or was just a risk that you are willing to take, given what the business needed? Yeah, it was a risk I was willing to take. You know, the business was really important to the business. They had never had long term contracts and and frankly, the resources needed to go through renewals year over year over year was just too burdensome and there was too much risk in the business. So it was just a decision and I made because it was something that was critical to the business. Gott, it's one of the things. You know, you you write a lot and talk a lot about motivation and about, you to the point, incentives and driving the right behaviors. You said that, I guess, when I asked You offline. You know, what's something that you have a controversial perspective on. You said that you can change behavior. Walk us through what you mean by that phrase. Sure you know. I think oftentimes in my career I meet a lot of people that say, you know, you're trying too hard to change the person to behavior. Don't don't bother people's behavior is what it is and you're not going to be able to change it and the personalities are their personalities. And I strongly disagree. And and that's part of the reason why I joined rocket trip, just because I love the concept of if you put the right incentive in front of someone, they will make a behavioral change and you just have to figure out again, what is that. So you know, even with rocket trip, when we say, you know, if you're eligible for business class and you downgrade to economy, you get to keep have those savings will in some cases that's thousands of dollars. Now, to a CEO that may not be worth it, so he doesn't make that choice. But to a salesperson they'll probably do it all day long. So again, I think. I think you just have to find what it is that motivates people and in sense people in the right ways to change their behavior. But I absolutely believe that you can change it. What's your point of view on on pips, on performance improvement plans to the point of changing behavior? Are they useful for you? And I'll I'll answer my own question and my experience, but I think my opinion may be changing, but in my experience I don't really like them that much because I feel like they create this sort of negative downward spiral where the person, but maybe I'm doing them wrong, where the person sort of feels like they're under the gun, they're under the microscope, and it sort of leads to demotivation. But what's your what's been your experience with sort of you've got those those people on the team that are not performing to the level that you need them to do? Use performance improvement plans or how do you think about changing their behavior to the point without, you know, changing the COMP plan for one person R versus the rest of the team? Yeah, unfortunately, I think performance improvement plans always come too late and at that point...

...we've probably already lost the person, unfortunately. But I think they're necessary because documenting that kind of you know what's needed and milestones and things like that are are important. But I think what I was referring to earlier about behavioral change. That comes way before you know a performance improvement plan. This is something that you notice early on and you take care of it and if you can motivate them in the right way and they can change their behavior, great. If they can't, immediately put them on a performance improvement plan. But I, like you, I haven't. I think it sends a negative vibe and so typically what happens is, even though I'm willing to work with the person and turn things around, I typically see that they are deflated and they are not feeling as if it's worth it at that point. So, unfortunately I haven't had a lot of success with them. We like to get somewhat tactical. As you can tell, I'm asking you know percentages on complaints, but if there's managers out there that are listening, what's the one on one framework that you have? How often do you think somebody should be meeting like if I'm a sales manager and I've got a team of six as, how often should I be meeting with them? What should I be doing in those meetings such that I can address any kind of behavioral issues or performance issues before requires a pip sure, so I'm a big documentation fan, so I don't believe a oneon one should take place without it being completely documented prior to and during, and a real easy way to do it is to use some document sharing like Google keep or something like that. But so that throughout and I do it once a week with with each ae and it's a thirty minute meeting and we both add different ideas and thoughts to the document throughout the week. Now, obviously if it's a if it's an emergency, it doesn't wait until the oneone, but these are things that are more strategic. So I use the oneone to basically address any challenges that they have and figure out ways that I can remove obstacles that are preventing them from being successful. So that's a big portion of what we talked about and how to how to move deals forward. And so specifically I'll call out one or two opportunities where I noticed that there's something missing or I might be able to help in some way because I have a contact that that I know that that's related to it. But we walk away with addressing each of our objectives and each of us during the week has one goal that we want to achieve in that meeting and we will typically not leave the meeting until that goal is achieved. Hmmm, is pipeline review that meeting or a different meeting? No, typically I like to do pipeline review in a group because I think people learn from each other with pipeline reviews and I think you establish the structure that everyone's operating on the same page, you're asking the same questions, everyone's working off of the same Matrix to assess risk in the opportunities and you know, we're sharing we're sharing information about what are some challenges that I'm facing? All, I'm facing that too. So I find it to be much more efficient to do pipeline reviews as a group or as a team. Gotta cool. You know, part of your management philosophy and sort of part of your leadership style is sort of a perspective on developing young talent, and so you've sort of talked about, you know, a framework for working with I guess we can call the millennials, but really they're the dominant laborers in the workforce now, so it's not as useful of a monarcher as it used to be. But talk to us about sort of like your perspective relative to conventional wisdom and how you think about engaging and motivating these these folks. Sure, I'm a fan of millennials and, and I'm not afraid to say it, I have many, many colleagues and peers that find the behavior of millennials of frustrating. You know, typically they're labeled as needy, entitled, they're not loyal, they're casual workers, and I frankly, have seen the complete opposite. I don't look at them as needy. I just think they need a lot of feedback and they want to build trust with their employer and that's good. I think that's a good thing. You know,...

...they do change jobs more frequently, but they're working and workforces where the mentality has been you get a salary and you work hard and be loyal. So there isn't this necessarily this culture of win win and making them feel good, and so it's no wonder why they're changing jobs more frequently. You know, the idea about entitled, if you look at a lot of the the recent more recent Harvard Business Review Studies that have come out about millennials and they're characteristics, they're saying that they work harder and longer hours than prior generations. So that's not even you know, that's that's another myth and people call them casual workers, but my experience has been that they're super ambitious, they're definitely progress oriented and again, if you look at some of the recent studies, thirty five percent of millennials the management positions. So they can't be they can't be that bad. So I think it's good. I think they're pushing the bar to cause companies to have more friendly, engaging, flexible environments, which is what we need in order to attract and retain the best health. Yeah, yeah, I agree. I think that's really interesting. So I guess to the point is it when you're engaging I mean, you know, millennials is again like the word is, so it's it loses a lot of its meaning because it's just such a large group of people. At this point, then a lot of people are not even millennials but are but are referred to as such. But as you're thinking about like attracting and retaining, is it just about incentives for you? What's the kind of work culture that you're building to make sure that you do engage the rising stars of the workforce and make it a productive place. Yeah, I mean, it's not about just incentives. So not at all actually. I think there's a large part of it that is about the culture and the level of engagement that you have with these employees, asking for their input, you know, letting them be a voice in the organization, especially if you if you see an employee who has a creative idea, let them speak it, don't speak it on their behalf. Invite them to an executive meeting, have them share an idea, give them some exposure and, you know, the best thing that you can do is give them some recognition. So I'm a big fan of the environment around them. Create one that that allows them to thrive and that that's not just motivating them with incentives. That's, you know, that's recognizing them and giving them that voice in the company so they feel like they're contributor. Yeah, I mean, again, I guess to agree with you. I think when I hear people talk about millennials, it just sounds like for the centuries old complaint of old people talking about young people. Does it doesn't sound particularly original, and it doesn't. It doesn't, sound, you know, particularly sort of like interesting from my perspective, and so I tend to agree. I think, you know, there's good people and bad people of every generation and there's lots of great workers and frankly, I appreciate that they're you know, this particular generation is open minded and wants there to be a mission, wants there to be a purpose. That feels residant to me and so, anyway, I'm on the same page. When you're thinking about like greats what here's here's a different question. Actually, you've been in leadership positions for a pretty long time at this point and and you've also been, you know, you've carried a bag and been an account executive. I guess one of the questions that for me always comes up is there's a difference between being an account executive and being a sales manager, and there's a difference between being a manager and a manager managers. What do you think? What does it mean to be a cro how is this cro different than a vice president of sales, for example, and what are the skills that you've developed that you think are are relevant for that particular title being compared to, you know, like a vice president title, for example? Yeah, I think CRO is much more engaged with the overall business as opposed to just the sales organization. So ahead of sales is typically thinking about you know, every day but tactical things. What do we need to do to close these deals? What do I need to do...

...to motivate my my people, whereas a cro is really looking at the entire business, the operation side of the business, the finance side of the business, product side of the business, and determining what strategy needs to get put in place, how is it going to be executed in order for the company to have the greatest chance of success, and so it's a much more strategic position. But more than that, I think I think it's a focus on the entire organization as opposed to just the sales organization. How did you learn to be a cerro what? How did you develop the ability to sort of think strategically and look across all of the interlocking parts of a company to drive effective change in growth? That's a really good question. I never I never thought of that, I think probably because I've been exposed to a lot of smaller companies. So I wore a lot of hats over the years. There were times that I was actually the HR person as part of mine, as part of my role running. We usedound like you'd be a great h our person. Some wouldn't argue that. I think always someone to argue. But yeah, I think. I think my exposure to all the different aspects of the business, because I've worked for companies when they were really small. I think that gave me a lot of insight and I definitely helped me think about the organization outside of just sales. For you, I mean again, your track record is pretty, pretty awesome, pretty amazing. How do you pick a company? What do you think makes a great company? I think first and foremost, as I said earlier, it's the people. I have to be feeling very good about the leadership team and the founder of the company, and I also have to you, a sense of connection to the to the board of directors. These are people that I will be reliant on. Their experience is typically great, their connections are typically great and I want to be successful, so I want to have those relationships, so I want to feel comfortable with them as well. And then I think it comes down to market opportunity and product fit with that market opportunity. You know, rocket trip is a great, great example of a company where there is a ton of upside. It's a fairly new concept. It hasn't really hit yet, but it makes so much darned sense and the market is definitely ready for it with this changing workforce. So I think it's about that. And then you know, not only is the market opportunity there, but does the product have the opportunity to meet the fit that's potentially out there to solve that problem? How did you do due diligence on the market opportunity before you join rocket trip, or was it just sounded big? Or did you talk to customers? You know, for those out there that are thinking about taking on new roles, what do you think they should be thinking about as they evaluate the opportunity and try to understand it more? Yeah, I mean you should talk to everyone you can. You should talk to someone on the board, you should talk, I'm depending upon the roll. You should talk to customers, investors, you should talk to other people in the organization. You know, I didn't just meet with some of the sales people. I also met with product people, Customer Success People. I even met with, you know, the develop the head of the development team, just to get a sense of the culture and make sure that you're aligned with with everyone. I think during the due diligence process with rocket trip, they did something really cool. They had me, they gave me a business problem that they were facing today and they asked me to come in and and present ideas about how to fix it. And it wasn't necessarily they weren't looking for for an answer, they were looking to see how I interacted with the rest of the leadership team, and I was looking for the same thing. I was looking for can I connect with these people? Can I work with them? How well are we engaged? And it gave me a really, really good sense of the kind of individuals that worked here, and I that was what solidified it for me. Was that that that event? That's fantastic. You mentioned having a good relationship with the board. What do you think makes a good board member and how do you cultivate...

...that relationship effectively? What do you think is appropriate? You know, and when you're evaluating a company based on the board, how do you what do you think makes a good board member? Yeah, I think first and foremost it has to be someone that is willing to understand the business. The problem I have seen in the past is that you get really smart people who have invested in companies had a lot of success, but they don't really understand your business, and so I always invest time to make sure that not only do they understand our business and the market, but they're really understand what our challenges are. So I think that's really important as far as managing them and having a relationship with them. Everyone knows this, but there should never be any surprises. Board members do not like to be prized, so be as transparent as possible and don't don't paint a prettier picture than reality. Make sure that they understand the potential risks, but don't pitch to them. They've already made their investment. That's not why they're they're they're there to help where they can, and that's why you should have a lot of engagement with them and keeping dialog alive in between Board Board meetings. I think is really important to when do you the true answer to this question is kind of right away, or maybe thirty days in. But from your perspective, given the sales cycle length at rocket trip, for example, when do you think it's really your number? You know you're in that board. Meaning is it? Is it right away? Is it three months in? At what point do you feel like, whatever the results are, they were a hundred percent your responsibility, or do you feel that right away regardless? Yeah, I think I think the expectations typically right away own it, it's yours. The reality is they give you a little leeway at the beginning, knowing that you're still figuring things out and experimenting, but that Leeway doesn't typically last very long. I've never seen it. Typically goes away after sixty days. But I think everyone's every my experience with board members is they're expecting that you own the number the minute you walk in, and so that's always been my my philosophy. So what if the numbers too big? Yeah, I mean that's something that you should spend time doing due diligence on before you join the organization and you will never know everything, but you'll have a good sense. There's no reason why you can't get historical numbers. Look at what has happened over the last couple years. If you have that much history and feel comfortable that the numbers are not so crazy that you you know there's no there's no way makes sense. It makes good sense. Last sort of like kind of question about about your career in some sense. Maybe it hasn't had an impact, any impact at all, but there's a lot of women out there that are listening. There is not, in my opinion, not on there are not enough women executives in sales specifically. Do you have any advice or did you have a specific way that you approached your career as a woman? or it never really occurred to you you were just doing the job and doing it as best as you can. Yeah, I'll tell you a funny story. This was back in two thousand. I had just joined my first startup and we were focused on banks, and so I was in count executive and I actually picked that vertical because I had sold a handful of banks and I said, wow, they're really responding well to our solution. Let's focus on banks. And at that time we were bringing in some new sales people and they had asked me to step up and oversee what's the sales organization and I had met with one of the things I wanted to do was basically find everyone in the in the whole region that I could find that sold to banks, soul technology to banks, and I wanted to start building relationships with him and I'll never forget that I had a meeting with someone who sold a technology solution to banks and he looked at me when I walked into his office and he said you're never going to make it. This is a boys book, this is a boys world. You're selling to banks like this isn't going to work. And frankly, that fired me up. I said there's no way, I'm that was like the words I needed to hear for the rest of my career. I wasn't going to let failure be a thing because I was a woman. So I've always had a very strong personality and have one of the strongest personalities in the room. I...

...think always worked in my favor. Not that you have to be obnoxious, but you can't sit back and, especially in a room fill full of men, you can't sit back and not be a voice. And rocket trip is actually the first company that I've been on the executive team and there's another woman on the executive team. So it's taken this long in my career to have another woman on the executive team alongside me. But I definitely think you know, after a while I didn't bother me, but those those words that I heard early on in my career stuck with me for a while and after a while I stopped caring or even noticing. But I think I think it's good to be aware of it, but it's less and less so the case. I think more and more women are stepping up and entering the workforce in really strong positions. Yeah, although for some people, you know, to your point, if you're naturally assertive, naturally confident, it's probably easier for you to sort of take some of that advice. For other people might be a struggle to, you know, try to be somebody that they're not as a means of getting to the executive level. But you know, maybe do agree disagrees. That just sort of what's required of an executive. So it doesn't really matter with your manner a woman. How do you think about that? Yeah, exactly. I I think it's more an executive thing than it is a male or female thing. I tend to think people that are in executive positions typically have stronger personalities. I never see, you know, I don't rarely see wallflowers who are executives. I just meant don't hold back. You know, if you're the only woman in the room, don't be intimidated and don't hold back that. I think it's great advice. WHO's the other woman? What position is she and on the executive team at rocket trip, she runs our customer support team. Okay, good, okay, fantastic. We're kind of coming to the end of our time together for now because we're going to revisit some great questions about why sales people don't achieve their quote on Friday, fundamentals. But what we want to do in this part of the program is just sort of pay it forward and talk about not just human mentors but also books that you've read. You know, key influences that you think we should know about because you think that they would make us better. So when you think about it, can be great people that have influenced you or can be great books that you've read about sales or about building businesses. What comes to mind for you? Yeah, I'll start. I'll start with the best book I ever read that I took so much away for, and that is extreme ownership. I don't know if you're familiar with it. That is the book that was written by Jocko will nick, who is one of the retired Navy seals and basically what he does is he shares real life experience from his navy seal experience where he applies the same principles that he learned to leadership skills and and it is very, very practical and there are a lot of things you can take away from it and it's super, super inspiring. I actually initially read the book and loved it and then I listened to the I listened to verbally to the book and it's at the audiobook him getting there. Yea, that it's actually Jocko who does it and it's way better than the book because you really really get to hear about these experiences through his through his own mouth. So it's a very cool, cool book. As far as stream owner shop, I love it. Yeah, well, you'll absolutely enjoy it. People that have been really inspirational for me. I had two previous CEOS who really were mentors to me and they still are today. One of them was my CEO Parmiter and one of them was my CEO at company share, and they were both a serial entrepreneurs, built businesses their entire lives and taught me a lot about the business side of companies. One of them taught me a lot about metrics and numbers and how important like never make a decision without them. And the other one taught me how important it was to invest in your people. I used to think he spent a lot on career development and he always has to tell me their your most valuable asset. You know it's it's almost never, never, enough that you can spend on them. So I did learn unless, unless it's travel, unless it's travel. That's true,...

...exactly, exactly, awesome, Kathleen. There's people out there that are listening that are probably inspired by just your track record, by your insights on sales and sales leadership, and you're probably more openminded approach to remote work and to how to motivate and manage people. So if they are, is rocket trip hiring? If they want to reach out to you, can they, and what's your what's how should they what's your preferred method of communication for strangers that want to connect with you? Yeah, thank you. Yes, we're always hiring, always hiring, and there's many positions open. You can check them out on rocket tripcom, but if you want to email me directly, you can email me at Kathleen Katchl em at rocket tripcom. That's fantastic. Kathleen, thanks so much for being on the show and I'll talk to you in a few days. Sounds good, Sam. Thank you. I team. It's Sam Jacobs. This is SAM's corner. Another fantastic interview. Kathleen Rombears what a track record she she joins companies and something good happens. So hopefully that's going to happen with rocket trip. We talked about a lot of different topics, but a couple things that I think we're actually pretty interesting. One of them is, you know, if you're out there in some kind of company that has a capped commission plan, that's wrong. Don't do that. We need an uncapped commission plan with really exciting accelerators. Now Kathleen mentioned that she thinks accelerators work best on an annual basis as opposed to a monthly or quarterly basis. I think that's probably pretty good advice, because we don't want somebody to get into the accelerators one month and sort of stock up their pipeline and then drain everything. But when you look at the you know, the consistent production over a period of time, you realize that they didn't produce what you needed. So think about accelerators on an annual basis. Now, when you're thinking about what's the difference between a vice president and a crow, Kathleen walked us through some of the ideas. One of them is you've got to develop a strategic perspective on the business. That's thing number one, and perhaps it's a little obvious. The CRORO, how is it different from the VP of sales? The Crow has responsibility for the go to market strategy, not just the execution of the sales team and the accunt of executives under their per view. And finally, she talked a little bit about board management. You know, the board can be sort of this mysterious, you know thing for a lot of us when we're joining these companies. They're not mysterious, they're just investors and they put their cop and l work. But what's really important, and somebody else taught me this, you know, many, many years ago, is there's this great phrase bad news doesn't get better with time, and that is that is the damn truth. So if you are presenting to a board, frankly, if you're presenting to your boss and you things aren't going well, you can't sweep it under the rug in sales. Listen, optimism benefits you a generally as a salesperson dealing with prospects, but optimism when it comes to managing expectations for your superiors does not work. When when it comes to managing expectations relative to the CEO, to your boss, to the board, we want to, we want to, we want to under promise and overdeliver and I know they might call a sandbagging, but we you got to really, really really focus on not not being too rosy in your assumptions, because the minute that you that they feel like you don't have a firm grasp of how the business operates, your job is on the hot seat. And that's also Scott Armor from next EVA from a couple episodes ago, talked about. You got to understand how. How did you hit the number and how can you hit it again, not just what? So a lot of great lessons. If you're going to be here in if I'm I don't know what that means, if I'm going to be in your ears and a couple days, I suppose, for Friday, fundamentals, definitely give it a listen. Kathleen walks through a number of amazing insights this upcoming Friday on why sales people don't don't succeed. So that's worth listening to. This has been a great show. Before we go, we want to thank our sponsors. That's Conga be leading end to end digital document transformation suite, go to go dotcomacom forward, sales soccer from our information. We also, of course, want to think outreach, the leading sales engagement platform. If you want to...

...get in touch with me, linkedincom forward, slash the word in forwards. Sam F Jacobs. And finally, if you haven't rated the show, please give it four or five stars. As I mentioned before. You know, if you think it's a terrible show, I don't know why you're listening. Maybe you sort of like gave it a chance because somebody recommended you. We don't want your rating, we want the rating of the people that are passionate net promoters. So if you do love the show, give us a four or five metal and sure that we can continue to stick around, that we rise up the charts, etc. Etc. And that's all I've got for now. Talk to you next time.

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