Scottsdale, AZ | GTM & Sales Leadership
GTM Builder. Revenue Leader. People-First.
15 years building, inheriting, and transforming sales organizations. I've started teams from zero and taken over teams that needed a reset - and in both cases, left behind something better than I found. I don't just build pipelines. I build people.
About Me
I'm Harry. Across 15 years in sales leadership, I've learned that the job looks different depending on what the organization needs. Sometimes that means building from scratch - no playbook, no team, no pipeline. Other times it means stepping into an existing team and doing the harder work: rebuilding trust, resetting expectations, and turning underperformance into a winning culture.
I've done both. My track record includes serving as the first sales hire at Object First, where I built the Americas team from zero to $30M+ ARR in three years before the company was acquired by Veeam. I've also taken over established teams in need of direction and turned them into high-performing, accountable organizations that people actually want to work in.
Outside of work, I'm a husband and father of two, a homeowner managing desert life in Scottsdale, and someone who invests seriously in his own growth - daily lifting, journaling, and stoic practice have been non-negotiables for nearly a decade.
Enneagram Type 8
Enneagram 8s are protectors, builders, and straight talkers. We move toward challenge, not away from it. We read rooms fast, take accountability seriously, and have a low tolerance for performance over substance. At our best, we bring a rare combination of force and care - the kind that makes people feel safe enough to grow.
I say what I mean and mean what I say. People always know where they stand with me. Directness is a form of respect - it means I trust you enough to tell you the truth, even when it's uncomfortable.
When I'm in a leadership role, the people on my team have a champion. I advocate for them, fight for their development, and take the hits so they don't have to. Multiple people credit working with me as a turning point in their career.
I don't need perfect information to move. I'd rather make a decision, learn, and correct than debate indefinitely. In early-stage environments, speed of execution is a competitive advantage - I treat it that way.
I raise the bar without tearing people down. I have high expectations, and I pair them with genuine investment in the people I'm working with. The best teams I've led have been defined by both.
I don't deflect. If something is broken under my watch, I say so and I fix it. Accountability isn't a value I talk about - it's how I actually operate. Teams trust leaders who take ownership first.
8s have a reputation for intensity, and it's earned. But what drives that intensity is care - for the mission, for the people, for doing things right. I invest in the humans around me because that's what good leadership looks like.
Leadership Philosophy
Whether I'm inheriting a struggling team or hiring the first rep, my first job is the same: understand the people in front of me. What's working, what isn't, and what they need from a leader. Diagnosis before prescription. Every time.
My job is to help people realize what they're capable of. I take the time to understand what someone wants from their career and figure out how to help them get there. The title doesn't matter - the human does.
Letting problems fester is a leadership failure. I address issues early, directly, and with the intent to fix them. Hard conversations handled with care build more trust than a hundred smooth interactions.
I carry my own bag. In early-stage environments I prospect, close, and build alongside my team. When people see their leader in the trenches, it changes the culture entirely. I've always led from the front.
GTM & Sales Architecture
Walking into an existing team means understanding what's actually there before making changes. I assess people, process, pipeline, and culture - then build a plan that preserves what's working and fixes what isn't. The fastest way to lose a team is to blow everything up on day one.
Bad outbound is worse than no outbound in a small, networked vertical. I spend time understanding the buyer, the competitive landscape, and real pain points before anything goes in front of a prospect. Reputation is a long-term asset.
The best reps I've ever developed didn't come in with a rolodex. They came in with hunger, self-awareness, and the willingness to be pushed. I can teach a sales process. I can't teach someone to care about the people around them.
Sequencing, CRM hygiene, qualification frameworks, onboarding ramps - I build the systems that let a team scale before I go wide on headcount. Putting reps into a broken machine just burns good people.
I've integrated AI tools into the sales workflow at Overtime to remove noise, improve prospecting precision, and surface insights faster. But the relationship, the read, and the close still require a human who knows what they're doing.
Experience
What People Say
Harry is committed to moving himself and the organization forward and will do whatever it takes to define and hit a goal. He leaves a sales organization that is based on high integrity.
Harry built the Americas sales team from scratch and drove significant growth. His legacy is that he was the start and worked tirelessly day in and day out to support the company and his team.
Harry cares about people first and foremost, and that human interest and caring is powerful in motivating his team to perform. He leaves a sales organization that is based on high integrity.
Occasionally, if you are lucky, you have the opportunity to work for someone that is more than a boss. More than a Manager or a Director. Harry Kurland, professionally and personally, exemplifies that "more." He treats you as an equal, takes the time to help you grow, and is a true leader within the sales organization. He is an asset to any organization.
Harry is the type of leader who has a lasting impact. He is never too busy for a conversation. Harry has a knack for effortlessly growing the people around him because he genuinely cares about the success of others. I am very thankful to have started my sales career with Harry as my leader.
What always stood out to me was Harry's leadership style - steady, supportive, and genuinely invested in the success of the people around him. He leads from the front, listens before he acts, and always makes time to mentor and guide others. Any team would be lucky to have him.
Passion, vision, and grit are core to who Harry is, and he embodies these attributes in his interactions with prospects, customers, his direct reports, and other leaders. He has the valuable ability to float between the weeds and the clouds. Harry is one of a rare breed of leaders. I wholeheartedly offer an unreserved recommendation of his work and his character.
I had the pleasure of working for Harry when I first started as an Inside Sales Rep. His passion, dedication and knowledge have made a lasting impression on me professionally. He taught me how to be a strategic and successful sales professional. As a sales leader, Harry made sure his entire team was equipped with the necessary resources and empowered each of us to be the best version of ourselves every day. Not only was Harry a great manager, he was a motivational mentor who challenged me to always be bettering myself and never settle. I can truly say that my successful sales career would not be what it is today without having the opportunity to work for him.
Let's Connect
I occasionally take on advisory and consulting engagements with founders and GTM leaders who are navigating the build phase - whether that's structuring a sales org for the first time, pressure-testing a go-to-market strategy, or developing the people already on the team. If you're working through something I can help with, I'm open to a conversation.