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About Me

DRIVING REVENUE TRANSFORMATION THROUGH STRATEGIC SALES LEADERSHIP, CUTTING-EDGE TECHNOLOGY, AI-POWERED INNOVATION, AND OPERATIONAL EXCELLENCE

Meet Chris Dickhans

As a global executive sales leader in enterprise software, I drive growth and operational excellence for SaaS, cloud, and hybrid solutions. With two decades of experience, I’ve built high-performance, data-driven teams that consistently exceed revenue goals.

I lead GTM and revenue strategies, leveraging technology, systems, and competitive intelligence to accelerate pipeline velocity, improve forecasting, and optimize sales cycles. My leadership has delivered double- and triple-digit growth, including propelling a PE-backed company to unicorn status in under 3 years and fueling 500% revenue growth in just 15 months at a startup.

As a highly engaged leader, with a hands-on player-coach approach, I deliver measurable results by increasing speed and efficiency, shortening proposal times from days to hours, embedding actionable intelligence into CRM systems to enable faster deal closures, and building customer success. I develop strong credibility and confidence in C-suite discussions and serve as executive sponsor to ensure alignment at critical deal points.

My approach blends strategic vision with operational rigor:

  • Redesigned commissions to support the shift to cloud subscriptions, protecting cash flow

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  • Developed value-based sales training to accelerate SaaS adoption; and effectively communicate and quantify benefits

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  • Streamlined thousands of SKUs reducing errors and cutting proposal time

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  • Embedded stage-specific CRM inputs for improved forecasting and deal speed

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  • Launched competitive intelligence programs and targeted campaigns, focused on value selling and competitive wedges, to increase win rates

I currently serve on the Advisory Boards of DeepXL Artificial Intelligence and Alakai Capital, expanding my influence across both advanced technology and commercial real estate.

I am recognized globally for hands-on leadership, I foster a culture of innovation, accountability, and empowerment. I believe great teams—empowered by research, data, and technology—can win in any market.

 

Notable achievements:

  • Built and led global sales teams of 60+  

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  • Established strong partner eco-systems for scalable growth

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  • Delivered 6x pipeline expansion in under 2 years (new offers, expanded markets, partnerships)

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  • Designed ROI-driven sales models boosting win rates by up to 80%

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  • Led digital and operational transformation across complex organizations

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I am dedicated to leveraging cloud technologies to drive measurable business outcomes for customers while building sales organizations that are efficient, effective, and relentlessly focused on customer success.

If you’re a growth-thinking leader, founder, or investor seeking to build robust revenue models and align technology with measurable business outcomes, let's talk!

My Story

I started my professional sales career in the insurance industry as a top property, casualty, life and health agent. I was the top sales agent for Jefferson County.  When I married the love of my life, who also worked for the company, I had to follow the existing HR guidelines  which would require one of us to step down.  Since I was less than two years into this career, and he held fifteen years, it was most beneficial for me to step into a new career.  This is likely too much information but it is important to understand my story - my personal journey.

I landed in a leadership role at Charter Communications because of the successes I had with Convergys - see Did You Know?.  At Charter, I wrote an RFI and RFP for an enterprise software need.  This is where I started getting interested in technology, best practices for deploying software, and offering ideas for software enhancements, etc.  After a year, I was requesting documentation from the vendor that didn't exist; so I began writing best practices documents and processes for enterprise deployments so that I could ultimately build domain expertise within Charter's leadership team.  I was sharing this documentation and ideas with the vendor and was quickly recognized as a thought leader with their platform.

 

It is at that time I started looking at opportunities in software and hired into my first software position at Witness, which was later acquired by Verint Systems.   While my first two positions were consulting for Professional Services and then moving into consulting in the Sales cycle, it was clear I was great at building relationships and selling the value of software in a world that sold features and functionality.   I stayed in this career for over fifteen years advancing every few years into four unique positions.  Each promotion during this part of my career was offered to me as I proved my loyalty, advanced my skills, and invested my time into building my professional career.

During 2017, I was referred to Calabrio from previous relationships that had transitioned to this fairly new software organization.  This position was not on the DNC (do not compete) list from Verint since it was just starting to get traction in the industry.  They needed someone to come in and build a strategic sales initiatives team.  At the time, it was a loose title.  Over the course of the first three years, the role morphed into Strategic Sales with its own P&L.  I was able to take this role into something nobody would have expected.  

Because it was a small - yet quickly growing - software company, I was able to spread my wings and share my experience to take on many roles where there were gaps that needed attention.  At one point I managed all these different functions as they grew into the company they are today.  Sales Analysts, RFx Team, Sales Demo Operations, Presales, Account Managers, Customer Success Managers, Operations, Principal Consulting (Sales and Professional Services), Implementation Strategy Team and, of course, Strategic Sales.

In summary, the last two decades have been a blessing in the software and SaaS industry and I can't imagine my career taking a different path.  I appreciate and value my path to success.

My Story - Chris Dickhans

My Clients

My Clients - Chris Dickhans

With over two decades of experience, I have had the privilege of working across a diverse range of industries. This extensive background has given me a deep understanding of each sector’s unique challenges and opportunities, enabling me to deliver tailored solutions and drive meaningful results in highly regulated, fast-paced, and/or rapidly evolving environments.

Healthcare | Hospitals | Insurance
BFSI | Financial Services | Fintech 
Banking | Credit Unions 
Telecommunications | MSOs | Life Sciences
Retail | E-commerce | IT
BPO | BPM | Outsourcing | Manufacturing
Transportation | Logistics
Education | Real Estate 
Hospitality Resorts | Hotels 
Legal | Compliance
Energy | Utilities
Government | Public Sector | FED SLED

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