Sapphire Ventures
Partnering with expansion-stage, enterprise software companies that we believe can become category leaders.
Sapphire Partners
Limited partner investing in exceptional early-stage venture fund managers.
Sapphire Sport
Partnering with early-stage companies at the nexus of technology and culture.
Menu close

Stephen Hallowell On Developing Sales Productivity With A Sales Enablement Team

Listen to the podcast
Stephen Hallowell On Developing Sales Productivity With A Sales Enablement Team
June 9, 2021 / 23:09 / EPISODE 6
Return to Episodes
June 9, 2021 / 23:09 / EPISODE 6
Return to Episodes

Episode Summary

Sales is the lifeblood of a company’s growth trajectory. However, when not properly executed, it can be a contributor for cost overruns and stalled growth. So what can you do to veer away from underperformance in your sales organization and achieve the results you should be getting? Stephen Hallowell of Highspot joins this episode to give us the answers. Having led major sales transformation efforts at some of the fastest-growing technology companies over the past several years, Stephen has the strategies to help us develop sales productivity in our companies. He discusses getting strong sales efficiency across your teams, understanding the importance of operating a best-in-class sales enablement team, and when you should think about starting a sales enablement function. Join Stephen in this conversation as he moves us deeper into the topic, guiding us with the wisdom to not only know what great looks like, but also scale it in sales.

Stephen Hallowell On Developing Sales Productivity With A Sales Enablement Team

On this episode, I spoke with Steve Hallowell. Steve has led major sales transformation efforts at some of the fastest-growing technology companies over the past several years such as Responsys, MuleSoft, Snowflake and now at Highspot. His roles have span sales enablement, sales operations and product marketing. He has a unique perspective on building a go-to-market engine that can support both high productivity and rapid scale. In this episode, we discussed getting strong sales efficiency across your teams, the core responsibility of a best-in-class sales enablement team and when you should think about starting a sales enablement function.

Steve, thanks for joining us.

It’s a pleasure to be here, Rico. Thanks for having me.

I’m looking forward to this conversation. I’d like to kick it off by getting to understand a little bit about your background, your career and experiences in the go-to-market space.

This is now my fourth company in the growth stage. I’ve typically joined in the lower tens of millions of revenues and then I scaled up from there up to $500 million and beyond. One of the defining elements of what I’ve been involved in is that, at least to my experience, each of these companies needs to undergo a significant transformation in its growth journey. A lot of what I’ve focused on is helping to lead that transformation process that helps us go from the early days of selling to innovators and early adopters to be able to sell to the mass market, sell based on value, challenger selling and the like and doing that from the chair of sales enablement, sales operations, sales strategy, leading those teams.

How many different sales methodologies have you used?

I’ve seen plenty. There are some common themes across them that it’s about finding the nuggets that are pertinent and typically, we’ve rolled our own based on the best of what’s out there.

Remix, reinvention of all the best elements of the ones out there. One of the things you’re working on is the strategic enablement framework, it’s a methodology or a blueprint. One of the things you and I talked about is nailing sales productivity linearity. What does that mean? How does that framework support that?

One of the things that has stuck out to me and this is both from the companies that I’ve been an employee of but also other companies I’ve had the chance to work with over the years. We all assume in our lives that things follow a bell curve, especially if that seller performance follows a bell curve where most people are in the middle. Yet the unfortunate reality for salespeople is that there’s often an awful lot more way off on the left-hand side of that curve who are not doing well. Maybe their attainment is less than 75% or less than 50% of quota, which is not a great place to be for them or for the company.

The implication of this if you’re trying to scale is big. It’s like you had a big V12 engine in your car, you’ve got this awesome big engine but only two cylinders were working. You’re dragging around this big, heavy thing and you’re not getting the performance. For companies, that big, heavy thing shows up in terms of expense. You’ve got a marketing and sales development organization cranking out leads and opportunities that land with reps who aren’t able to close them. You’ve got a bunch of reps who are taking time from sales leadership. You’ve got SC, technical sales time. You’ve got other specialist time, that’s all being wasted because you’ve got a big group of your organization that is struggling to perform at the level they could.

When I see this, it’s a sign that the organization hasn’t figured out how to take what the best people are doing. What is working to sell this product? What are the things that we know to be true and helping that broader base of people do it? Instead, they’re relying on we’ve got some capable people. Maybe it’s that they’ve been at the company a long time. Maybe they’re exceptionally talented. Maybe they have phenomenal territories. It could be any one of those things. We’re allowing there to be a situation where some people are either lucky or exceptionally smart but that’s not something we’re able to scale. If you’re trying to scale a business from whatever size you are to something much larger, you want all those cylinders firing as effectively as possible. That’s what this framework is designed to do is to say, “How do you help get that consistent performance across your team?”

What are usually the failures in those cylinders? How do they manifest themselves in a company? How do you correct those?

It comes down to two things that are simple to say but hard to do in reality. It comes down to one, have you gotten clear about what you want your people to do? That sounds like one of those things, “We know what we want our people to do.” Maybe you do in an implicit way but is it written down and documented at the level that somebody else can follow it? Just because 1 or 2 salespeople or your senior executives know what great looks like, that doesn’t mean it’s in a form that you can scale yet. Often, companies don’t get specific enough about what they want their teams to do. This doesn’t mean trying to create a paint-by-numbers environment. This is not a takeaway all the thought from the reps. There’s still a tremendous amount of thought that has to be done but you don’t want to ask people to reinvent the wheel over and over again when there’s simply no good reason to do that. That’s where you get a lot of errors in this.

Let’s say you wanted to get a bunch of people to climb a big mountain, take your mountain of choice, whether Mount Rainier or Mount Whitney on the West Coast, Mount Washington in the East Coast, under some challenging circumstances, like right now in February 2021. If I told people, “Top of the mountain is that way, go figure it out,” probably my success rate wouldn’t be high. On the other hand, if I give them a map and the right clothes, the right training, and the right gear in terms of how to navigate the situations in the winter, my success rate is going to be a lot higher. Those people still have a lot of hard work to do. They still have to climb the mountain. They may have to figure out how to get across icy snowfields on their own but at least we’re setting them up for success versus making them figure it out from scratch.

The equipment in this example would be playbooks, video training. What have you found to be the most effective training mechanisms for sales teams?

That touches on the other half of the framework. You asked about the failure modes. One is that we’re simply not clear with the team about what we want them to do. The other is we don’t have a systematic approach and process for helping embed those behaviors in the team. We’re not helping the team master the things that matter. There are about four layers to that. The first layer is, have you written down what you want people to do? Is it well-documented? Is it clear? Do they have the resources and tools, be that sales facing assets, decks, discovery guides, background on their customer? That would be the analogy I’ve given you, the map, the field guide, the ice axe, the jacket and told you to go, “Go have at it.” For most of us, that’s not enough. If you asked me to climb Mount Rainier right now with just that, I would not do it. I would say, “I’m not putting my life at risk. I would want to practice with that special gear and build confidence in a safe place.” The training piece is about good training should break down a complex concept especially if you’re trying to understand your product differentiation or understand a persona that you’re engaging in their challenges. How do I break that down into small pieces, make it easy to understand it and help people learn in a structured way?

Training shouldn't always be easy. If training is easy, it's probably not adding a lot of value. Share on X

The other piece of that is having structured practice. Most of us learn by doing, we want to try things in a safe environment, we want to get feedback and then once we’re feeling confident then we can go out and do it in the real world. Often organizations don’t provide enough structured practice that the reps say, “I get this, this makes sense to me. I feel good about doing it in the real world.” It stopped somewhere short of that. There’s this confidence divide that folks have to bridge. The next layer after that is if you don’t manage to it, if there’s not an expectation in the field that we do this. You could give me all the training in the world, you can give me all this stuff. If I’m nervous about this, I might keep delaying the day. I’m going to try that hike for a long time. If you say, “Steve, we’re going to pick a date, we’re going to pick the customer. We’re going to do it together. I’m going to be there to coach you. Let’s try it.” I’m going to get that done. The next piece that companies tend to miss is sales management engaged in driving these things. Does that frontline sales manager know it’s part of their responsibility to drive these things? Do they have the training in terms of how they coach it?

There needs to be tight alignment with those frontline sales managers to make sure that they’re also communicating what you mentioned. One of the other areas I wanted to focus on is the role of sales enablement. It can be nebulous but that responsibility of the framework in those four levels to execute on them is the sales enablement team. Can you give me through your eyes and your experiences what the role of sales enablement is? How does it work most effectively within an organization?

If you go back to these two pillars of defining what great looks like and then scaling great, define the winning behaviors, help people master the winning behaviors. Classic sales enablement is going to be over on the right of helping them master winning behaviors. The tools in the toolkit are typically I work with marketing and build content. I can make that available. I can run training. Sometimes organizations over delegate to sales enablement and say, “Sales enablement is going to fix this problem for me.” Without recognizing the role that sales management needs to play in there as well and creating a strong interlock there. The table stakes for sales enablement are driving those first two pieces.

The next level of strength is that they’re going to be pushing to engage sales management and building the sales manager enablement and have that tight interlock with sales leadership to drive those things. Having a point of view on what do people inside and outside of the enabling team need to do to drive these behaviors. The next level after that is this more strategic side of helping to define what great looks like. This is something that sales enablement can’t do by themselves. You need sales leadership, it’s marketing leadership, it’s enablement and ops has a role to play as well to get clear about what we want the best people to do, but somebody’s got to lead that charge.

The reason that the company so often don’t do this well is you look across that group of people and no one of those people feels accountability on a daily basis to get it right that often the sales leader would be a natural place to go. A sales leader, with all the right intention and can get caught up in the day to day, they may not be as comfortable operating in a zone of, “Let me step back and build some frameworks around this.” Architecting that plan. Marketing leader might be a little stronger there but often the marketing leader is removed from the day-to-day of the sales conversations. One of the places that strategic enablement can play a big role is to quarterback that effort to make sure that work is getting done. Pulling the right people into workshops or discussions to drive the organization to have a clear view of what exactly do we want our people to do so that we have something that the rest of the more tactical enablement team can help scale and drive.

It’s a challenging role to be in sales enablement because working in sales is stressful. You’re measured quarterly. It’s obvious if you did good or if you did not do good. You have to make these enablement activities, whatever they may be, easy. Not so it doesn’t look like it’s impeding on their job, if anything, helping to accelerate it. Are there any ways to make it easy? Maybe one of those ways is integrating it with sales management so it becomes one. Are there other ways to make it easy?

When I think about making it easy, first off, I want to make it as easy as possible for your sellers to do what you want them to do. That means taking friction out of that process as much as possible. That’s things like can they find the material they need? Are there clear examples of not necessarily the CEO or the head of sales that appear doing what you want them to do where they can look at somebody and say, “That person is like me. They’re not somebody who’s special. I can replicate that. I can copy what that person is doing?” That’s the foundation in making it easy. Sometimes you’re going to need to push the rep sometimes and that’s okay. Training shouldn’t always be easy. If training is easy, it’s probably not adding a lot of value. If you need to have training, if you say, “We have a gap.” It’s okay to make that challenging. People will probably respond better if that’s challenging than if it’s something where it’s they say as a layup, “I don’t need to be doing this.”

There’s a little bit of a trap in making it easy. We want to take friction out where friction is an impediment, but if we have some meaty skills to develop, that’s going to require challenging training, challenging practice, and real accountability. That’s the only way those pieces are going to come together. We want to make sure that everybody along the way, whatever job we’re asking them to do, is clear and straightforward in terms of what that asks us whether that’s AE or that’s a sales manager that is asking to inspect and coach these activities.

That’s a great description of it. Also, there needs to be some level of accountability. How do you create accountability around a lot of these resources? To run an enablement program, it is expensive in some cases. It is resource commitments where resources are inherently scarce within a startup. How do you create accountability to make sure that everyone is executing the vision you set out?

The clear thing comes back to having clear goals and knowing what you want the team to accomplish. You may start with an objective like we want faster onboarding but it’s important that the enablement leader and the sales leader are able to dissect that a bit and say, “Why is onboarding too slow? What’s the place that people are struggling?” A commonplace might be, “New hires are slow to build pipeline.” You say, “That’s something that’s tangible now. That’s something that I can measure and I can look at quickly.” One of the things that we did at MuleSoft and I replicated it at Snowflake, I’ll give a sudden permit over MuleSoft credit for pushing me to do this, which was we built out a dashboard where we knew for every new hire, 2 months, 3 months, 6 months, 9 months, what should their pipeline build look like?

We were able to see who’s red, who’s green and if somebody was in the red then that prompted, I would have somebody on my team have a chat with their sales manager, diagnose it. What’s the issue here? What do we need to fix? Some of these were one-off things like somebody got their territory too late or somebody’s STR pairing wasn’t working out well. Sometimes there are things that we said, “We’re not systematically enabling people on the right stuff. People are struggling thematically in a commonplace. We need to build a program to fix that.” You have to be anchored on something concrete that you want the team to do. It’s got to be concrete enough that it’s actionable and you can measure it.

Visibility is key. If you can’t measure it then you can’t fix it. The example you used there is getting to first principles. Onboarding is too broad of a thing to tackle with an initiative. You need to have the pain point to identify what initiative to point it out. A lot of companies are in this growth stage and sales enablement isn’t there from day one. From your experiences doing this multiple times at a few companies and now in your role enabling sales enablement teams, when do you think the right time is to start this organization within a startup?

When you get to around 1 dozen to 2 dozen sales reps is about the right time to do it. I’ve usually been hired too late. I’ve typically been the first enablement hire and gone on to build that organization and it’s usually too late. It’s at the point that there’s a lot more catch up and retrofitting things in ways that if we got it right in the first place, we’d be better off. If you go earlier, it can be tempting especially in early stages, to say, “We want somebody who can run a little bit of training.” That’s one of the less important pieces early on because you don’t have the scale that demands rigorous and consistent training. Your managers can do that. At that stage, you’re learning how to sell, you’re learning what that best path for selling your product is and what that motion looks like. The ability to have somebody with enough sales experience and ability to think abstractly and package things to help you accelerate that process of codifying what the best people are doing and then helping to disseminate that across the team, how you accelerate the organizational learning of the company as you’re learning how to sell your product is one of the best things you could have in a first enablement hire.

Somewhat being like the detective to identify the winning playbook, the winning strategies that you can then implement. Don’t assume that you know it before you hire that sales enablement person because you’re probably, at that point, still getting anecdotal evidence is what I’m pulling out of this.

Maybe the head of sales knows and it’s natural for the head of sales but head of sales doesn’t usually have time to write that down and codify it in a way that all the folks you’re hiring can then replicate it. The other thing I find that’s common in many fields is that somebody who’s second nature doing something is often not great at teaching. They do it naturally. They don’t know how to communicate clearly, “I’m doing this for this reason.” It often takes a partner to work with them and ask them questions like, “Why did you do it that way? Why not do it this way? Tell me more about that.” That act of packaging and crystallizing whether it’s the head of sales or a top AE is doing so that you can then scale it is one of the pieces that is often missed.

I like to end these conversations with the question a little off the beat of what we’ve been talking about. We had a lot of mountain analogy. I don’t know if you climb Mount Rainier. What’s your favorite hobby and why do you enjoy it?

Companies need to have clear goals and know what they want the team to accomplish. Share on X

I love getting outside and being active. Whether that’s running, cycling, hiking, that’s my place to go blow off steam and how I manage stress and stay healthy. A good day for me is when I’ve gotten some good big exercise in. I haven’t gravitated towards the big mountain climbing, I’m not a technical climber. I’m more of an endorphin versus adrenaline in that way. I do think something like Mount Rainier could be a lot of fun to do someday but I have no aspirations for something like Everest or the big mountains.

The endorphin versus adrenaline thing, I do those activities for the same reasons especially now, it’s critical to get outside since we’re all always inside and our surroundings aren’t changing as much as they used to be when we were in a different environment. Steve, I want to thank you for your time. This was a great discussion. If people want to get in touch with you, what’s the best way? Is it LinkedIn?

LinkedIn is great. They can also shoot me an email, [email protected]. I’d be happy to chat.

Thank you so much for the time, Steve. I look forward to having more discussions.

Thank you so much, Rico. It’s good to talk to you.

Disclaimer: This article is for informational purposes only. It is not an advertisement, and it is not intended to provide advice or services of any kind, and does not constitute an offer to buy or sell, nor a solicitation of any offer to buy or sell, any security or other financial instrument in any fund sponsored by Sapphire Ventures, LLC (“Sapphire”). The information contained herein is not an investment recommendation, and may not be relied on in any manner as, legal, tax, or investment advice. While Sapphire has used reasonable efforts to obtain information from reliable sources, we make no representations or warranties as to the accuracy, reliability, or completeness of third-party information presented within this document or survey itself. All metrics presented are derived from survey respondent answers only, whereby no outside sources were used in compiling the index. Metrics presented do not in any way represent official statements by Sapphire. Various content and views contained within this article and index represent those of the survey participants only, which do not necessarily reflect the views of Sapphire. Such views are subject to change at any point and do not in any way represent official statements by Sapphire. No guarantee of investment performance is being provided and no inference to the contrary should be made. Past performance is not indicative of future results.

About Steve Hallowell

Steve Hallowell is the Vice President of Strategic Services at Highspot. Before Highspot, he led Sales Enablement, Strategy, and Ops teams at Snowflake, MuleSoft / Salesforce, and Responsys. Steve is focused on helping revenue organizations reach their full performance potential. He has particular experience in helping sales teams transform themselves to meet the demands of hyper-growth.

Steve works closely with Highspot customers to help them use enablement as a strategic growth engine. He is also active in the broader enablement community as a speaker, advocate, and mentor.