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GTM Navigator is our ongoing series where we break down the essential components of nailing the right go-to-market strategy.

In this episode, Stephanie Perez, Managing Director at Fin Capital, speaks with Kathleen Waid, Fractional CRO. Kathleen brings a wealth of sales and go-to-market knowledge having spent her career across Enterprise Software Sales and GTM roles including CRO of NeuroID (former Fin portfolio company, acquired by Experian), CRO of Prove Identity, VP of Sales and GTM at PointPredictive and VP of GTM at Fiserv.

In this episode, you will gain insights into how to build best-in-class sales training and coaching, from onboarding, to playbooks and promotions. We are grateful to Kathleen for sharing her insights and we hope that this episode of GTM Navigator empowers you to build and strengthen your sales organization.

Key Questions Discussed:

Transcript (edited for clarity):

Welcome to Go-to-Market Navigator by Fin Capital, our ongoing series where we break down the essential components of nailing the right go-to-market strategy. Today, we’re diving into sales training and coaching with Kathleen Wade, former CRO of portfolio Company NeuroID and fractional CRO. Hope you enjoy.

Stephanie Perez (00:23): Kathleen, so excited to speak with you on this particular topic. We’ve gotten to know each other very well across several of our sales leadership roles, and I’ve always been extremely impressed by how you challenge yet nurture the teams beneath you and so I wanted to spend our time today digging a bit deeper into how you do so. I think it would be really valuable to folks who are just stepping into those sales management and leadership roles for the first time. So with that, happy to get started.

I think my first question is really around setting up folks for success. What are some of the best practices that you’ve seen for how to onboard a new sales rep into an organization?

Kathleen Waid (01:03): Yeah, so that’s a great question and thanks for having me. First and foremost, I think culture is paramount. Onboarding a new sales rep is not about just jumping into the product, the process, the company. You have to set a tone of authenticity and a tone of comfort. You really want to establish that cultural vibe that’s going with the company and bring the salespeople into that. You as a leader will set that tone on culture. I think that’s where you have to start. Every time I meet somebody new, I don’t say, tell me about your background. I say, tell me about you. Your resume looks great, fantastic, but I want to know what’s important to you in life, right? I think when you onboard anybody, but in particular salespeople who tend to be very outgoing, they want to get to know the company, they want to get to know you as a person, as a human, not as a leader. And you just have to set that right tone.

Once that’s established, it’s making sure they understand how the organization works. I don’t dive right into product. I don’t dive right into all the “what’s” of the training. I dive into, let me tell you how the organization works, what’s working well, what we can improve upon. And the last thing I’d like to do really early in the process is say, “Hey, you’re brand new here, so you’ve got fresh eyes. You haven’t started ‘drinking the Kool-Aid’. What I really want is a feedback loop on what you see in a very protected environment, what you see that the company can improve upon. What can we do better in your onboarding process or in our sales process, or how we communicate about our value proposition, whatever it may be”. So really making that two-way communication street open from the get go. And then you just move into the standards. You should have a training pack. You should have something that is consistent that you walk people through. You should have some trials along the way, some places where people get checkpoints, 30, 60, 90 day checkpoints. But it all starts for me with establishing a good culture that folks feel comfortable to communicate in a very open way.

Stephanie Perez (03:12): Let’s dig a little deeper into that 30, 60, 90-day plan. What should that look like?

Kathleen Waid (03:17): What I really like to do is just have measurable checkpoints, 30, 60, 90. 30 days could be let’s just do a one-on-one pitch with a sales leader and the new sales director. Just do it in a really comfortable, safe environment, pitch me the product that you’re selling, let’s go through a discovery call, I’m going to give you some real time feedback and maybe I’ll write some feedback up. We’re going to record it, but this is your practice run. After 30 days, I would expect you to at least to be able to have a practice run. You should have your territory known, you should be starting your initial outreach to your territory. Maybe it’s a percent, you should cover 10% of your territory with an initial outreach. So goals at 30 days, everything should be measurable. There’s a little subjective element to everything that you do, but salespeople, we love our numbers. We love to know that we’re meeting a goal.

Something like 60 days, you want to probably think about having a wider audience for another go at a discovery mock call. An environment where it’s not as safe, but you maybe have a peer group that are also participating in it, they have role play, and you’re getting some real time feedback. And if you’re in sales, you should be pretty thick skinned and you should want that constructive criticism. So let’s just widen the audience. I’d also have other targets. What are you doing top of funnel? You’re early on, but are we seeing new activity top of funnel? So depending what product you’re selling, the price that you’re selling it for, you should have, if your first stage is called discovery, you should have a certain either number of opportunities or dollar of ACV dollar values at that top of funnel.

And then the same thing for 90 days. You should want to see a little bit of pipe progression going from discovery to maybe qualification, whatever your next stage is. So I’m seeing you start to move some things through the funnel. You should have a certain number of discovery calls that is supported by you or by a sales leader. By 90 days, you should be able, depending on the product, to start running a little bit on your own.

Stephanie Perez (05:24): That totally makes sense. And I know this is a bit nuanced depending on how technical the product is or what segment it is that you’re servicing, but what does a typical ramp period look like and what are the expectations during that ramp period? And also how are you compensating folks for that period of time?

Kathleen Waid (05:42): You hit the nail on the head. It depends on the product, right? So ramp period depends on how long your sales cycle is. And first of all, how do you define ramp? Is ramped meaning that I’m sales productive, I’ve closed my first deal, or does ramped mean that I am fully trained and enabled and empowered to go out into the market to build my pipeline? First of all, when we say ramp, we have to define what ramp means, and it varies by organization. I work with a lot of different companies now, and terminology is really important. It is sales cycle dependent. If you’ve got an 18 month sales cycle, that implies that it’s a bigger dollar sale, it’s a more complex product, there are more decision makers in it. For an 18 month sales cycle, I would expect the ramp period, meaning the time that I can go out and be individually productive, not close a sale, to be 90 to 120 days. And actually you should measure this. This shouldn’t be just a guess. It should be something you’re measuring through your CRM through other people who have come through as new sellers. You can put down a stake, but move your stake depending on what you’re actually seeing, however you define ramp in your CRM. If I’ve got a 90 day goal of having $2 million in my top of funnel discovery stage, how often did I meet that in the past, right? Am I setting the bar too high or too low? So, when I think about ramping and onboarding and bringing people up to speed, make sure that you’re measuring your past to set the right stake for a performing seller.

Stephanie Perez (07:30): Changing gears here, we’ve talked a little bit about sales training, but tell me what sales coaching is and how that’s different. Because they are two very different things and oftentimes, I think they’re a bit confused.

Kathleen Waid (07:46): Training for me is the what, meaning what product are we selling? What market are we in? What are the industry pain points? What’s our value proposition? What are our differentiators? That’s training: understand what we do. I think coaching is more about the how. How do you communicate effectively? How do you ask the right questions? A lot of times, I’m saying the same thing over and over again. We as people like to answer questions when they’re asked of us, but really the best sellers ask a better question. They ask to understand. They don’t always answer. So coaching for me is real time feedback, listening, digesting, and it’s more about how. Coaching is about enabling people to work independently, to work their own territory, empowering them through advice and skills that maybe they can fine tune, and then just holding them accountable to doing it. Training is about what: things you want them to know. And then coaching is just all about how: the execution.

And it’s always subjective again, to how I might sell and I try to take that into account. My personality comes through in how I sell, and I try to encourage that in all sellers, just be you, be authentic, be natural, let your personality come through. And so how do you incorporate that in making sure that your personality does not overpower it, you really want them to come through authentically in how they sell well, but also give them some good coaching guidance or tips or constructive criticisms to improve upon.

Stephanie Perez (09:34): Giving them the kind of enablement skillset to be able to be the best they can. And both are continuous, right? And you’re always iterating on both those things, both training and coaching.

So, for companies that are at that stage where they’re growing their sales function and they’re looking to really graduate or advance individual contributors into leaders or managers within their team, how do you help do that?

Kathleen Waid (09:59): The structure that I’ve used and I like to use is really player coaches. So it is not all of a sudden one day you’re an individual contributor and the next day you’re a leader of a team. I like to do a little dating before we get married, right? Let’s give a person an opportunity who we think has leadership skills, who’s ready for it? Let’s give them a segue to do it. You still carry your own quota, but now you have a small team that is part of a larger quota. You have an override number, but you’re carrying your own bag and you have to balance carrying your own bag as well as coaching and supporting your small team, two or three reps. Again, it depends on complexity of the product, average sales cycle dollars, all that good stuff. But a player-coach is a nice segue and you set it up that way. No surprises. Our goal is to have you be a player-coach in the next six months, 12 months, whatever it is. Here’s your goals and objectives during that. We want to see you close one million dollars in these 12 months for yourself and then two million as a team. So three million total, you’ll be compensated properly. That’s the target. If we meet that target, guess what? We’re going to be hiring more salespeople, then we’re going to need to graduate somebody (hopefully you) to the full leadership position. But the goals tied to the additional hiring, which ties to the formal promotion to leader outside of moving on from player coach to just coach. So there’s a pathway, it’s not mysterious, you lay it out and there’s numbers associated with it. In sales, you do try to hire in advance to meet the market demand, but you’ve got to make your revenue numbers. You’ve got to make your bookings in order to justify more sales, and if people understand what the road looks like, they’re going to travel down it and then they’ll earn the formal promotion because they delivered.

Stephanie Perez (11:57): You touched on people that are delivering. What about those that are struggling and are not delivering? What does an improvement plan look like in a sales organization?

Kathleen Waid (12:07): Before you write an improvement plan, you should know what you want the outcome to be. You can write an improvement plan where you know you’re going to exit this person, it’s just not a good fit. You can write an improvement plan where the person just has not been performing. They have the potential, you want to motivate them, but you also need to cover the company. You need to know what your end goal is in writing the plan. Let’s say your end goal is to get this person productive again. They could have something going on in their personal life, they could just have a down time. You want to pull that out and support them as best as you can, as well as making sure the company’s meeting their objectives.

So once you write it and you know what your stated objective is, then for me, everything’s numeric. You have to decide how long do I want this plan to be? 30, 60, 90 – everyone just assumes it should be 90. Nope, it could be 30. Decide how long, and then decide on your goals. Am I talking about pipeline progression? I want to see a certain number of dollars, a certain number of deals move from one stage to the next. Am I talking about a challenge of top of funnel? You’re not doing anything in your top of funnel, so I want to see new top of funnel dollars. Every plan should be super custom based on the outcome you’re looking for and what you’re trying to achieve with your pipeline or with your bookings.

Then when you give the plan, have just an open conversation with the receiver of the plan of what they want the outcome to be. It’s not an easy conversation to have, but I’ve had them where people are like, yeah, this is definitely not the place for me. And that’s okay. Sometimes it isn’t the place for the salesperson and they should move on, and you want to give them a soft way to do it, and you want to be supportive. But I think people avoid that conversation because a hard one to have. But I like to ask the salespeople, what do you really want the outcome to be? And nine times out of ten, they’re very honest with you. Now, there are some of those cases where people are like, no, no, I definitely want to make it work out and then they don’t put any effort in. But in most cases, especially if you have an authentic relationship, you’re going to get the real deal and then you’re going to work with them to the exit plan that you both agree to.

Stephanie Perez (14:30): Well, that’s a great thing about being in a business where your work is quantified in some manner. You have very clear metrics by which to assess success and improvement.

Touching a little bit on making this a part of the company culture and the culture of the particular team and the processes and the systems by which you operate, how do you ensure continuous training? Is it something that you revisit on a quarterly or annual basis? How much time should a leader spend thinking about something like this?

Kathleen Waid (15:04) Let me start with how much time and how you even decide. It should be part of your CRM or it should be product or market driven. I would never say there should be training every quarter. I remember early in my sales career, I had a sales manager who forced us to fly to the west coast (I’m on the east coast) every quarter for training, regardless if it was needed or not. And frankly, it was just a waste of time because it was dictated at every quarter we’re going to meet. It was unproductive and I always keep that in mind when I think about when we’re going to conduct trainings. It should either be product or market dependent or launching a new product, or we need to have a training on a new product, new features, new differentiators. It could be market driven, a competitor starting to really throw a lot of shade in our direction and we need to address it. So that’s market driven, there could also be new regulations that change the market and that will change our pitch. So I never have a steadfast rule in anything as it comes to training. I also like in any training to talk about what we think has worked in the past win-loss reviews, especially if it’s an add-on to a product.

But I would say your CRM should still be the source of information on when, what if it’s not new product. Let’s say you’re stalling in a certain stage in your sales cycle and you’re noticing the average days in that stage continue to expand. Let’s say you’re having a proof of value, proof of concept, and the time just keeps expanding –  that’s a time for not only training but discovery. What’s happening? Do we have a product problem we have to address? Do we have a training issue where we’re not presenting the POV concept right? Do we have an execution problem? So always keep your CRM data really close, and that will help you dictate if it’s a training issue or if something bigger is happening outside of sales control that you need to drag in other people in the organization and say we got to band together and fix what’s happening here because we can’t have our POVs continuing to drag on, it’s holding back revenue.

Stephanie Perez (17:22): You touched on CRM and the GTM Tech stack has gotten so bloated. There are so many different point solutions that solve for very specific aspects of the sales cycle and stages as well. Curious if there are any particular vendors out there that you think are extremely beneficial in terms of enablement, whether that be for training or coaching, the likes of Gong and others, are there any in particular that you would suggest to some others?

Kathleen Waid (17:49): You’re not going to like my answer on this one. My answer is no, because this tool stacks that are out there, I think are very product dependent. In the companies where I’ve either been a CRO or I’m a fractional CRO, we are using very different tools depending on the particular product. So I don’t celebrate one above all. I do think that just like when you’re selling and when you’re buying, you have to understand the value added and the ROI on purchasing this solution, whatever it might be. But I’m not a firm believer in any one product.

Stephanie Perez (18:32): Yeah, no, that’s definitely a fair answer. And I think what we’ve seen is a lot of bloat when it comes to that particular vendor selection process and who folks have onboarded. Wonderful. Well, this was amazing. Thank you so much. This was so helpful. I think it’ll be extremely valuable to folks that are really taking on these new leadership positions and thinking about how to enable their organizations for success. And you’ve done this many times, so we very much appreciate you sharing your insights.

Kathleen Waid (19:00): Well, thanks for inviting me and Fin Capital love working with your companies, so I appreciate it.