An uncommon skill mix for finding new perspective
Executive Experience
25+ years in venture-, private equity-backed, and publicly traded businesses
Listening Seat Time
Hundreds of interviews (1000s of hours) and 1:1 conversations for inquiry and research
Coaching Training
Listening and activation training of a professionally certified leadership coach
Since 2019, Highland Insights has worked with category-leading consumer and B2B leaders and their investors to ask different questions, start better conversations, and access insights they can take action on for measurable impact.
We offer the intentional inquiry, focused listening, and pattern-recognition capabilities of an outside resource who can see and hear things that often go undetected in day-to-day business building—and then we put those insights to work. As action-oriented, and collaborative operating executives, we understand how to get things down with others in a growing company—by engaging employees, demonstrating progress, and stoking confidence, creativity, and communication.
The result is the uncommon combination we set out to create—a partner that can help clients uncover new perspectives and then integrate them for real impact in real-life settings.
ABOUT THE FOUNDER
Robert Morton, PCC
Robert has spent the better part of three decades understanding customers, building brands, and crafting customer experiences as an executive for standout companies.
His travels have taken him across industries, from the Motley Fool to education software leader Blackboard, where he led marketing as a member of the exec team, to venture-backed consumer e-commerce startup Territory, which he built from the ground up as co-founder, CMO, and Chief Customer Officer.
That diversity has continued in his consulting and coaching work where he’s collaborated with leading companies and investors in the consumer and B2B technology realms.
A graduate of Georgetown University’s acclaimed Leadership Coaching program and an International Coaching Federation-certified coach, Robert coaches leaders and investors building growth-stage businesses as well as executives navigating major professional transitions. He’s also served as a Board Director in the non-profit and venture-backed software arenas and proudly coaches leaders as a member of Truepen Coaching’s leadership coach network.
When he’s not helping companies and leaders build better experiences and grow, he’s likely to be hanging out with his wife and three daughters, heading to a functional fitness gym, hiking somewhere, sitting in a sauna, or relaxing in a really, really cold body of water. A mirth-seeker at heart, Robert loves reading and writing about (and trying!) the various ways to increase and improve wellbeing.
“
In consulting and coaching (and life more broadly), I’m pulled along by a deep curiosity about two questions.
What progress are people really trying to make?
How can we help them see their world differently to make that progress better?”
”
—ROBERT MORTON, FOUNDER, HIGHLAND INSIGHTS“
Customers, employees, CEOs, board members – when it matters most they all trust Robert’s insight and judgment. He is singular in his ability to push people, companies, and brands towards a more authentic mode of connection—one that’s more meaningful and equitable and more profitable.
”
Matt maurer — CMO, ICFLatest Posts
“
Robert came to us highly recommended by a number of colleagues, took on a potentially sensitive topic – a 360 review of me the founder/CEO by the leadership team - to increase trust and communication among our rapidly growing team, culminating in an all day offsite he led that was universally positively received.
”
—Bo DAVIS, FOUNDER & CEO, MarginEdge
WHAT’S IN A NAME
The story behind Highland Insights
As a half-Brit, Robert has been visiting the north of Scotland for many years. Like in other regions with highlands, Scotland hikes feature many a moment when you’re emerging from the trees and a whole new view suddenly opens up before you.
Our name is a nod to that experience and the purpose that pulls us along, helping people find a new angle on their situation—for their customers, for their organization, and for themselves—to uncover new paths for growth.
“
What I found most useful about my coaching with Robert was understanding that I have agency over how I approach a situation / problem / relationship / habit. It has been life-changing to stop and consider the different paths that may lie in front of me at any given point and that there is almost always more than one path.
”
—ANJU OLSON, VP STRATEGIC PARTNERSHIPS