Building an Enablement Team from Scratch: Where Do You Start?

Head of Sales Enablement at Slack, Nikki Curtis, joined the team in December of 2017 to build out their Sales Enablement department. With a proven track record of building teams from scratch at companies like Salesforce and LinkedIn, that is once again Nikki’s goal at Slack.

For Nikki, there’s a certain thrill from building a team from scratch. Every company is different, and there is no doubt that this time around with Slack there will be new and difficult challenges along the way, but that’s all part of the fun.

“The biggest factor that influenced my decision to join the team at Slack is the opportunity to empower, enable, and support the amazing trajectory that we’re on. That’s what my role is designed to do.”

“Whenever you’re starting a new challenge, and you get in there and look under the hood, it’s always more than you expected – but that’s expected,” says Curtis. “The priority, company-wide, is how we align and build infrastructure for growth. I tend to think about this differently than others, and so for me it’s not about what kind of skills we need to add, but what the right infrastructure we need to build is.”

6 months into the new role at Slack, Nikki has made real progress towards developing a strong foundation for the Sales Enablement team, but there’s still a lot to build. Here are where her priorities stand today:


1. Onboarding

“Our sales team doubling this year both in North America and Internationally. How do we ensure that the growth we’re experiencing doesn’t make us bust at the seams?”

2. Communications

“How do we optimize the internal process so there's clear channel management of what the right information is to give the right teams at the right time. It sounds simple on paper, but it’s actually very tricky to get right.”

3. Skill Development

“We’re investing in a culture of coaching. That starts with allowing managers to have the bandwidth to focus on skill development with reps.”


With the Sales team at Slack set to double this year, the number one priority for Nikki is to build an onboarding process to get reps set up to sell successfully as soon as possible. From empowering reps with the content they need to sell, to providing guidance through the use of different playbooks, and everything in between, arriving at a successful onboarding plan is an lengthy process.  

“How do we ensure that the growth we’re experiencing doesn’t make us bust at the seams?” says Curtis. “If there isn’t a smooth onboarding process built out, it can create a lot of unwanted distractions.”

“This is the priority I’m really excited to work on – building out and testing mechanisms to ensure that our reps are customer ready.”

Serving Existing Reps v.s. Onboarding New Ones

“At Slack, the sales organization is going to double this year and that’s why onboarding is a primary focus. It’s the one program that we can not get wrong this year.”

“In a hyper-growth phase when you’re hiring a ton of people, it’s crucial to be mindful of the cost and strain it has on an organization. Now, if you're at a point in the organization where the headcount isn’t growing at a fast-pace, that’s when more investment and focus should be put on optimizing the existing team.”

If you compare Nikki’s current role, to her later days at LinkedIn (after the company had scaled the Sales team) the focus looks very different.

“There wasn't that much growth at LinkedIn anymore, so my time was invested in product innovation rather than rep growth. Of course, we were always invested in developing reps, but there wasn't the need to put significant time into onboarding because we didn’t have the kind of net new hires coming in that we’re experiencing at Slack.”


Communications is more of an overall theme that includes a number of initiatives:

  • How can we, as an organization, remain tightly aligned internally about our product go-to-market strategy?

  • How do we, as the Enablement team, work with the Product team to ensure reps are getting the information they n8eed in a timely way?

  • How does that information get turned into actionable tactics to start communicating to clients?

  • How are reps kept up-to-date with changes along the way?

“We take advantage of our own platform for a lot of these things – everything is coming through different Slack channels we have set up. The focus now is optimizing the internal process so there's clear channel management.”

“The dream we’d like to eventually get to is delivering the right information, to give the right teams, at the right time. It’s simple on paper, but it’s tricky to get right.”

Ensuring Sales Enablement Doesn’t Become a Distraction

In the relationship between Sales Enablement and Sales, there’s a fine line between Sales Enablement being a helpful resource and a distraction. What is it that Sales is focused on most? Selling. But, in order to do that effectively, they need to be kept up to date on things and have continuous training. So the question is how create a healthy balance. For Nikki, she believes it starts with some sort of foundational tiering system.

“Tier ones are critical information. Every manager and rep needs to made aware and trained on them immediately. Then, say a tier three is more of an awareness piece. Everyone should still be made aware of these things, but it’s not essential information that requires extensive training.”

“Once you’ve got your tiered system in place, it’s time to think about the delivery mechanisms. Tier ones will likely be in-person meetings, compared to a tier three that can be delivered only to Sales Managers and be passed onto individual reps from there. Finding out what works and what doesn’t is important to find out early, so spend a lot of time testing.”

Now, things get even more complicated with the type of growth Slack is experiencing. The product is evolving so much, so quickly, how do you manage the communication with Sales? Book multiple meetings per week to catch every rep up on product changes as they happen? One big meeting each month to try and capture everything that’s happened? Are these in-person meetings or communicated through internal messages? Is the entire Sales team in one big meeting or is it broken into groups?

“I'm a big believer in A/B testing. Coming into any role and thinking you're going to have all the right answers, right away, is the wrong mentality because every organization is different.”

Knowledge Management

Like most problems we have in B2B SaaS, there are tools to help alleviate some of the pain and automate parts of the process. For Slack, they use Guru to manage content internally as an easy way for reps to find information they need, when they need it.

“We’ll be re-launching Guru internally soon so that we’ve got a solid infrastructure loop for information,” says Curtis. “If you want to enable the Sales team to sell to buyers—who in today’s world are more educated than ever—you need infrastructure for them to get the information they need quickly and accurately.”

Skill Development

“Something that remains important to us as an organization is investing in a culture of coaching. With that, we’re aiming for our managers to have the bandwidth to focus on skill development with the reps.”

“That's where our best chances of scaling quickly and effectively comes from. Empowering managers, giving them coaching guides, and train the trainer sessions will allow us for the one-to-one skill coaching that is so important in the longevity and success of the company.”

Scaling Sales Managers with Sales Reps

Scaling the headcount of sales reps gets the bulk of attention when companies are scaling, but what about their managers? When a company is growing the Sales team, the majority of hires are junior reps, and so a strong set of managers that can develop your reps are essential.

“One of the main reasons Slack brought me in is my belief and passion for the empowerment of  frontline managers. It’s something that can’t be forgotten for a company that's growing,” says Curtis. “Sales managers are an under-appreciated role in many organizations, but they make a huge difference in the success of failure of a growing company.”

“Sales Managers in many ways are the backbone of a Sales team. One topic I talk to Sales leadership a lot about is how we can continue to develop the culture of coaching at Slack, and Sales Managers are always a key part of that conversation.”

“An example would be an Enablement team going from office-to-office doing a half day skill development workshop on discovery. That workshop can be helpful, but the skills talked about for that half-day aren’t going to get ingrained unless Managers are continuing to preach it day in and day out with their reps. That's where the magic of rep development happens, continuous coaching. That’s how you build a culture of growth.”

Bonus Tip from Nikki: Remain Transparent from Top-to-Bottom

No matter how much you believe top-down communication and transparency, it’s hard to remain that way as you grow. It’s not because anyone is trying to hide anything from anyone, but because things are moving fast. When things are moving fast, people forget to communicate as much as they should.

When this happens, it can create a level of tension between reps, management, and executives, because no one is clear about what they are looking for from the other parties.

“When you’re operating quickly, transparency and communication can get lost, especially when things are going well in the business. Things move so quickly that reps lose track of what’s important to sales leadership at the time. There’s no bad intentions there, but it’s just something that happens.”

“People start assuming things instead of asking questions about what information leadership is most interested in or what data they’re tracking most closely. It’s stuff like that, that needs to be clearly communicated so everyone is operating towards the same goals.”

“It’s something we’ve run into at Slack, because—this sounds cheesy—everyone is so nice. No one is trying to hide information or anything like that, but we’re operating so quickly that we forget to ask the questions we should be or taking the time to make sure we’re all aligned. That’s something we’re working on, trying to slow down and take the extra steps to ensure everyone is brought along on the journey.”