How Motive’s Sales Team Has Evolved for Growth

An inside look at Motive’s sales team culture, and how it enables team members to help clients find the tech they need.

Written by Taylor Rose
Published on Feb. 27, 2024
How Motive’s Sales Team Has Evolved for Growth
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Every few weeks when Kathleen Osgood was young, she and her brother had a chore that many people take for granted — trash service. The two would go outside and swing bags of household trash up into the bed of an old F-150 pickup truck. Once the truck was full, they would drive down the rural roads that led to the dump. Their house wasn’t in an area where trash trucks could easily reach them. 

“The fact that a trash truck comes to my driveway once a week these days feels like a luxury,” said Osgood, who now works as a strategic account executive on the enterprise sales team of Motive, a tech company that creates products meant to improve the safety and productivity of the physical economy. 

“We are currently working to solve a very important challenge in the waste services and recycling space that I am really passionate about,” said Osgood, noting that with this project, “Motive is in a unique position to reduce accidents.” 

Motive’s platform was initially used by commercial trucking to track and automate fleets. The company recently went through a rebrand to show that its platform and tools can expand beyond commercial trucking. Today, Motive uses IoT hardware and AI to serve industries like oil and gas, food service, construction and more. 



A study conducted by Motive reported that in 2023 five clear challenges impacted the physical economy, according to 1,000 industry leaders that the company surveyed. The team at Motive believes that AI can help address some of these challenges. 

  • 59% cited the challenge of rising costs
  • 51% pointed to economic instability 
  • 45% listed labor shortages and talent retention 
  • 42% cited supply chain disruptions  
  • 36% pointed to operational inefficiencies



Expanding Roles 

To support the changes at Motive, the sales team has grown. Enterprise Strategic Account Executive Michael Williams has witnessed a lot of those changes. 

Williams was one of two enterprise account executives at Motive in 2017. Today, he is one of more than 40 who are managing 15 accounts. 

“Things have changed dramatically, but our market fit has grown. I have been a top-producing AE most years in the company,” said Williams. 

Williams’ role is to manage large opportunities, seeing them through from discovery to implementation. Part of that means that Williams is in charge of maintaining the executive-level relationship while customer success team members manage the day-to-day relationship with the specific users on the account. 

“I am responsible for building a pipeline, building champions and working large, complex deals to signature,” said Williams. “I oversee sales representatives in pipeline generation, partner with sales engineers on strategy and preparation, then lead a trial success team, working through complex legal processes to get a master service agreement signed.” 

Williams then helps with the handoff to customer success. “After that transition, I continue to develop additional expansion and growth opportunities in the account,” he added. 

Being a part of the rapid expansion of the customer-facing teams and helping to build out the onboarding process led Williams to mentor and help new employees duplicate the steps. 

“I’ve never had support like what I experience at Motive,” said Williams. “It is second to none. Presale, trial, technical, product, executive, legal, implementation and professional services — everyone is invested in my success. It’s truly amazing. Not to mention, our product team is the best in the business.” 




Part of Osgood’s role is to interview safety and operations leaders to understand how Motive’s technology might be able to help them.  

“I spend time with safety and leadership teams, teaching them about our technology and how we solve challenges in the physical economy,” she noted. “In turn, I learn from them and provide this feedback to our product teams to ensure we stay on the cutting edge and are solving real-world challenges.” 

Osgood takes the feedback she receives and shares that with Motive’s product team to help pilot the company’s solutions in the field. 

“It’s awesome to see our clients’ eyes light up when they realize we can be such a meaningful partner,” she added. 


“It’s awesome to see our clients’ eyes light up when they realize we can be such a meaningful partner.”


Osgood sees her role as an evangelist for Motive in emerging markets. Her work on the enterprise sales team allows her to collaborate with some of Motive’s largest prospective customers.  

“I love getting to solve big challenges,” said Osgood. “Some of my projects can take months, even years, and the relationship I get to build with our clients during that time is one of my favorite elements of the job.” 

Enterprise Account Executive Jessica Demarest is also responsible for seeing prospective customers through the entire sales cycle. 

“My time here has been a mix of learning a new industry and executing a blueprint for success when it comes to ramping quickly in a new sales role,” said Demarest. 


Rising to the Challenge 

Demarest joined Motive in the fall of 2023, but already has experienced wins and losses. 

“The biggest challenge in a new sales role is building a pipeline,” she said. “We have fantastic resources here at Motive. Having such a strong team around me has helped me exceed my ramping expectations and build my pipeline to three times my quota.”

The flourishing sales pipeline hasn’t come without challenges, though. Demarest addresses barriers — like finding the right contact who is interested in taking a call to talk about Motive products — by meeting goals for leading indicators that kickstart her pipeline plan.  

“If I meet my leading indicators in the first four months, my pipeline will lead to closing significant new-logo businesses in months five and on,” she said.

Demarest’s pipeline plan includes checking off leading indicators like booking new business meetings, booking demos, starting trials, creating visible opportunities over $200,000 and conducting business-value assessments.

“My philosophy when it comes to pipeline generation is to go directly to the top,” she added. “I’ve had success in getting to the economic buyers and then doing a multi-threaded campaign with other stakeholders in the company.”

For Osgood, there is a common challenge that prospects share regarding time. 

“There is a lot of disjointed technology in the physical economy — lots of point solutions that are typically not well integrated,” she explained. “This is a burden for clients and users of this type of technology. It can create decision fatigue when thinking about making a change.” 

Osgood went on to explain how there is often hesitancy from prospects about the time it takes to install a new tool in their tech stack or the learning curve that is required. 

“I get it,” added Osgood. “Change is hard and everyone is busy these days.” 




All of the challenges that the enterprise sales team faces at Motive are worth it when they can help a client. 

One of the recent wins on the enterprise sales team had a nearly year-long journey before choosing to commit to Motive. Williams told the story of how this win ended up being the largest single account for Motive, bringing in over 8,000 vehicles under contract.

“It was incredibly complex and it took a large team to win the deal and continues to take an even larger team to manage the implementation,” noted Williams. “The fruits of our success resulted in being awarded another massive expansion.” 

Williams referred to the sale as a “huge accomplishment and testament to the support the client received during implementation.”

She continued, “I started working with my champion for over a year before the opportunity became a request for proposal. Even after the request for proposal and being awarded the business, we moved to an eight-month trial of 300 units.” 

The trial period brought its own challenges with hardware and software. Motive had to keep a team connected to the customer daily to ensure success. The team was able to make the trial period successful and establish confidence with the client. 

“I learned that if you develop strong relationships with your decision makers early and continue to invest in those relationships, you build trust that results in true partnerships,” said Williams. “The win was a huge contract, a huge logo and continued expansion with additional growth opportunities for years to come. Personally, it was a true marquee logo that I am proud to be a part of.” 

For those in the market for customer success roles, “The opportunity is massive at Motive,” said Demarest. “The ability to sell an industry-leading technology — that actually has real business impact and can help make it safer for us all to drive on the roads — is empowering.”


Read MoreWith a New Name and Big Growth Plans, Motive Aims to Evolve the Physical Economy



Responses have been edited for length and clarity. Images provided by Motive Technologies.

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