Commercial Talent: A CRO Playbook for Success

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Dean is a sales and marketing development leader, delivering solid results in sales and go-to-market execution, with extensive experience implementing growth strategies and operational measurements, developing solution selling skills and building trust-based customer relationships. His success is driven by his ability to hire and develop team members, quickly improve team productivity, and implement opportunity, account, and territory control best practices that achieve operating and financial targets.

Q. When you’re at a networking event, how do you describe your independent career status, and the value your expertise brings?

Sales and Market Development. I help software companies develop and maximize market opportunities through talent recruitment and development, operational best practices and impactful solution selling techniques.

Q. Why do you think there is increasing demand for independent expertise with PE operating teams?

PE operating firms are accustomed to leveraging outside financial and operations expertise. They are now leveraging sales and market development expertise because many go-to-market teams still need to develop strong solution-selling and relationship development skills. They are thus struggling to sell value and develop champions which are essential to growing deal sizes and managing forecasts.

Q. Describe a recent or successful assignment in terms of scope, duration and any particular highlights in the outcomes.

One of my prior clients was led by a founder/CEO who had never worked in another company and had no reference as to how a CEO should support the sales and marketing team. He did not understand or value competitive compensation, new hire onboarding, quota setting, territory assignment, minimizing channel conflict, high-quality sales tools, and a defined sales process and playbook. In short, he was afraid to let go and trust since much of his identity was tied to the success he had winning the company's first Clients. He felt that no one could do it as well as he could do it. He was probably right, but this was not scalable. Moreover, the sales team was reluctant to leverage his vast talents.

Working with him to define the characteristics and attributes of the ideal sales professional, showing him how his peer companies incentivized sales performance and how they operationalized the sales process, all supported by key measurements, gave him confidence that he could let go. Sales turnover was all but eliminated, deal sizes increased by 35%, deal volume increased from approximately 30 deals/quarter to over 50 and the average quota achievement increased from 60% to 105%. Plus, he was now able to focus on strategic requirements including product development, acquisitions, and partnerships.

Q. What advice would you give to anyone about to embark on an independent career as to how they can provide the best results for a client, while fulfilling their own career path?

Focus on listening, learning, developing trust, and establishing measurable outcomes with your Client sponsor.

Q. What's your favourite thing to do when you're not on the clock?

Flyfishing and exploring the waterfalls of the Blue Ridge Mountains with my golden retriever.

Looking to leverage a unique mix of market and analytical expertise? Engage with talent like Dean by posting a project now, or by talking to us about how to build up a pool of similar talent in the field.

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