We had the distinct privilege of sitting down with Nikki Curtis, Head of Sales Enablement at Slack, to talk shop. It became immediately apparent to us that with Nikki, ‘talking shop’ meant discussing what she’s most passionate about enabling her people to be their best.

An identified “corporate teacher,” Nikki comes from a family almost entirely made up of school teachers, including both her parents, brother, sister-in-law and aunts and uncles. Teaching is in her DNA. After a stint in Washington D.C, she packed up her life and headed to the tech capital of the world, San Francisco, and landed an entry-level sales role at Salesforce, which jump-started her “corporate teaching” career and love of technology.

ONE:  “I basically, for lack of a better word, hustled”

Nikki’s passion for Sales Enablement was ignited when she started winning internal competitions for best presentations, best customer stories, and who was best at selling The Message at Salesforce. She wanted to share her success with her peers and didn’t let the lack of positions available stop her.

“There actually wasn't a role in sales productivity at Salesforce and so I basically, for lack of a better word, hustled.”  She met with everyone on the team who might one day become her boss and asked for homework to help her level up.   “I did all this research on LMS systems because that's really the only interface you had for the sales team’s onboarding. I would always volunteer to help during these training sessions and about six months later, my boss responded — I've never had someone pester me more, we'll give you a job.”

Nikki’s drive led to her rapid success — by her mid-twenties, she was running global onboarding during a hyper-growth period at Salesforce. She stepped into that role when the existing instructor went on mat leave. Twice a month, anywhere from 50 to 150 people would attend onboarding classes, and when the opportunity came up to fill the leadership gap, Nikki leapt at the opportunity.

She’s continued to flourish and evolve since.

TWO: “Invest in the person, not the numbers”

As an enablement leader Nikki cares about two things:

  1. How do we protect salespeople's time
  2. Empowering the sales team to hit their targets

The two go hand in hand.  As Nikki puts it, “If you really invest in the person they feel so much more invested in the end result. They feel invested in the team, they feel invested in the company, so they're naturally going to work harder. They're going to produce more.”  Allowing people to feel like they're doing it for something greater than themselves will produce that push within the team.

How Nikki invests in people matters just as much as the goals of her organization. To put it into context, Nikki found that she could achieve productive authenticity by prioritizing the individual and being transparent with data. To this day, this approach enables her to have open and honest conversations with the people who learn from that data and are ultimately responsible for executing effective strategies based on that learning.

“I go very much back to data. That's where I live and breathe. What's going to give us the most revenue, where are we going to  see the biggest impact and when you're talking in those kinds of terms, if you take the emotion out, then it's really easy to get there and your folks know, "  Alright, hey, if our goal was to get this much adoption then we're all just gonna brainstorm on how we get there and it's not gonna be personal. It’s not about whose idea we pick or don't pick because it's really around what are we going to see to get the best result."

However,  if you only invest in the number, people start to believe, "Alright, it's every man for themselves.  I just have to hit my target," and then they're not invested in the whole company — that's when you get a lot of turnover within the sales organization.”

[bctt tweet="“If you really invest in the person they feel so much more invested in the end result. They feel invested in the team, they feel invested in the company, so they're naturally going to work harder.” – Nikki Curtis, @Slack" username="kiiteHQ"]

THREE: Invest in building the right infrastructure

According to Nikki, newer enablement teams tend to sway towards the cool or trendy thing, such as discovery training or negotiations, which are very valuable initially but don’t add any longevity to the enablement strategy over time. The way she tells it, there’s a lot of excitement and energy when reps hear about big deals closing; it's not about minimizing that energy, it's about empowering it by building on momentum.

At Slack, for the first two quarters, Nikki is focusing her time into getting the right process in place, building right operational rigour, and investing in the right tools so that she’s enabling her team for the next five years.

“I'd rather have a lot of the "behind the scenes" work initially to set the right platform for us to grow in a really meaningful way.”

In other words, to go fast, you must first give yourself permission to go slow enough that you do it right.

“If we don't do our due diligence to build that, then we don't have the right foundation to grow.  It's really important and it's something that often times gets overlooked because you're being told, "We need them to hit a number."

It’s important the reps get the information they need first, so they know what they should be selling and how they should be selling it before they can finesse the art of the sell.

FOUR: “Show up as authentically as you can.”

In her article, Six years of human development,  Nikki describes going from a management style of pushing too hard to human-to-human coaching and allowing ownership within her team from her time at LinkedIn.

We asked Nikki, What key piece of advice would you give a new manager looking to change their management style?  Her answer: Show up as authentically as you can.

“Find your authentic voice and allow the people on your team to have an authentic voice.  Thankfully, once I really started to open up about how I was feeling and where I saw my faults, it made me so much more human.  Then we really bonded, they became really invested and the dynamic changed and I realized, just as I need to look at myself as an individual, I need to see each of them as individuals.”

The best work anyone can ever do is when they feel their most comfortable and when they have the freedom to be their authentic selves.

[bctt tweet="Find your authentic voice and allow the people on your team to have an authentic voice. — Nikki Curtis, @SlackHQ" username="kiiteHQ"]

FIVE: Work Smart, use Slack

Nikki describes working at Slack as, “One of the most wholesome sales cultures I've ever been at, and it's so refreshing.”  

Stewart Butterfield, CEO of Slack, really believes in the principle of — “you come in at eight or nine and you leave at five and when you're at work, you don't get distracted by a ton of stuff.”  You work hard, and when you go home, you go home. Slack aims to bring teams together, make sense of their work, and ultimately make communication more fluid and people more productive.

“What's great about Slack though, it's not like an email where you've pushed information. When you communicate in Slack, there's an opportunity to have a dialogue on it.  Folks can type in and ask questions, they can really engage with the information and I think that's the biggest productivity tool from an enablement side.”

Sales Leaders use Slack to work smart. They engage with the information being shared by reps, learn from their questions and resources being shared, and watch conversations unfold in real time. That’s how their leaders know where their teams need more support so that they invest in the right attitude, programs and people.


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