Setting Clear Expectations & Fostering an Entrepreneurial Culture with Niki Phillips, Sr.Director of Sales at Hootsuite

10/10 GTM Episode 46
Transparent sales process - working together
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Welcome to Season 3 of 10/10 GTM: The Podcast for Revenue Leaders!

Our guest for Episode 46 is Niki Phillips, Senior Director of Sales at Hootsuite. She brings more than a decade of sales experience to the conversation.

In this episode, Ross and Niki discuss why setting clear expectations, communicating on progress, and fostering an entrepreneurial culture are key strategies for driving execution excellence. 

Listen to the episode here, and get the key takeaways from our conversation below.

Set clear expectations 

If you want your team to be successful, you have to be crystal clear about the expectations from the get go. Start by asking and answering these questions: 

  • What are the goals?
  • How are we going to get there?
  • What happens if we don’t get there?
  • What’s expected of the team daily, weekly, monthly, quarterly, and annually? 
  • Who’s responsible for what?

"As leaders, our job is to ensure everyone knows exactly what they’re working on and toward," says Niki. "Without clear expectations, confusion and wasted time occur — and in sales, every minute is precious."

For example, if your mission is to move upmarket and secure bigger, better deals, you need to define success for your team. This includes deciding how much time to allocate to smaller deals, how to de-prioritize them, and what actions to take. Then you need to set clear targets for increasing average deal size, identify key account types and industry segments to focus on, and outline those to avoid. All these details must be clarified to set clear expectations with your team and gain executive support.

Religiously communicate on progress

Oftentimes, leaders track progress in their heads. While they may know what’s going on and where the team stands, this information needs to be disseminated across the team so everyone understands the specific goals and how they’re measuring up. 

“Hootsuite is a quarterly business, but my team is measured on weekly KPIs,” says Niki. “At any given time, the team knows how we’re performing against our goals, and we report on it religiously. We meet every Monday to review the numbers and focus for the week. We discuss what needs to be course-corrected and ensure everyone understands what’s expected of them and why.”

Religiously communicating progress removes assumptions, creates transparency across the team, and gives everyone the chance to course correct as needed. “Clear expectations bring order to chaos,” says Niki. “Because my team knows what topics we’ll address each week, their KPIs, and the importance of not moving or canceling key meetings, it helps everyone stay on track.”

Foster an entrepreneurial culture

When you provide your reps and managers with a solid framework to build upon, and then allow them to develop it as if they were building their own business, you create an entrepreneurial culture that empowers your team to take control of their destiny.

Niki believes this approach drives better results. “Culture is king," she says. "When you give your team the autonomy to own their roles, decide how much effort they want to put in, and ultimately determine their own earning potential, you empower them. Of course, you need to establish guidelines, set KPIs, and define revenue targets, but at the end of the day, it’s about creating an environment where individuals feel they have the freedom to innovate, take risks, and push boundaries."

A word to the wise: fostering an entrepreneurial culture will be a struggle if you don’t set clear expectations from the start and consistently communicate progress. These strategies go hand-in-hand, and when implemented together, they enable your reps and managers to take on more responsibility without the need for constant micromanagement.

“I give my reps the leeway to work on accounts that interest them, instead of just bestowing a book on their desk,” says Niki. “They can get creative. Of course we have guidelines in place and playbooks for them to follow, but I also encourage them to take ownership over their work. In my experience this leads to better results and gives my team exposure to new skills they can build on.” 

About Niki

Niki is the Senior Director of North American Sales at Hootsuite, where she oversees all net new revenue in the region. She has over 10 years of experience in SaaS, startups, and team leadership.