Howard Doherty

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A progressive data-driven senior sales leader with a bias for action and year-over-year success, Howard puts tech companies on the map. An inclusive, empowering developer of people and teams, he drives revenue and profitability for emerging tech startups and more established brands. An expert in building sales organizations from the ground up, he creates infrastructure, establishes sales plans and pipelines, and identifies new markets and opportunities, positioning firms for a successful exit. A charismatic, transparent, and persuasive communicator, Howard builds trust and buy-in with ease and excels in delivering business value.
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Recent Posts

Outsider Insights | The Backup Plan You Don't Have Is Already Costing You

Outsider Insights | The Backup Plan You Don't Have Is Already Costing You

Fri, Aug 21, 2026 | Posted by Dawn Werry

Executive Takeaways

  • Commercial team gaps happen for many reasons: someone leaves, someone is underperforming, or the business needs a capability the current team doesn’t have.
  • Mid-sized companies tend to run lean, which means there’s rarely a qualified backup ready to step into a critical role.
  • The real cost of that gap isn’t the empty seat. Priorities slow, teams lose direction, good people get frustrated, and commercial efforts stall.
  • Rushing a permanent hire isn’t always the answer. Fractional resources can keep the business moving while you make the right long-term decision.
  • The best time to decide how you’ll handle a critical commercial is before one opens.

Outsider Insights

Across Chief Outsiders, we talk to hundreds of CEOs every month. In this series, we explore the trends and challenges we’re hearing from these discussions – and what you can do if you’re facing the same issues in your business.

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