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A Blueprint for a Successful First 100 Days as a CSO

April 15, 2021

Contributor: Gloria Omale

Sales leaders should use a five-phase approach during their first 100 days to deliver quick wins, build credibility and successfully transition into their new role.

Stop and slow down. That’s the No. 1 piece of advice from chief sales officers (CSOs) to their newly minted peers. And it’s the hardest thing to do in a world reeling from pandemic impact and tectonic shifts in buying behaviors.

“We heard that advice time and time again during our many conversations with CSOs,” says Maria Boulden, Vice President, Executive Partner at Gartner. “They said they wish they had taken more time to be thoughtful and strategic in their planning when they first stepped into the role. As one sales head put it, you have to ‘go slow to go fast.’ That’s especially true now.”

With the myriad challenges, opportunities and targets a CSO has to deliver and an often-innate driver style, it’s really easy to be all speed and no vector. Too often, new leaders take on more than they can handle and commit to change before understanding their internal and external ecosystems, including what the world needs from your company as well as the company’s people, processes, politics and priorities. 

“Your first few months are critical. They set the tone for your tenure,” Boulden says. “It can be hard to rebuild trust and turn momentum back to positive if you start off on the wrong foot. And that’s especially true now.”

This is the case whether you’re a first-time CSO or a seasoned sales executive joining a new organization. For a smooth and successful transition, follow these five steps during your first 100 days: Prepare, assess, plan, act and measure. 

Download guide: First 100 Days: A Guide for New-to-Role Heads of Sales

Five key phases for new-to-role CSOs

Phase 1: Prepare (Days −10 to 15)

As a new sales leader, the first 100 days are full of opportunities to make rushed mistakes with long-lasting performance implications. Instead, take this time as a great opportunity to learn about the customer ecosystem, the organization, your peers, the commercial function, the products and your team. Decisions will certainly need to be made during this time. The world moves too fast to get a 3-month break from the commercial sprint. It’s how you make those decisions that will also set the pace for your leadership cadence and style.

Regardless of your professional background, this is your best chance to gather information about your new role and organization. Mitigate the risks of your transition by clarifying the mandate for the role and business priorities. The initial (and very brief) “honeymoon” period presents a high-leverage time to advance your agenda. So plan carefully, but rapidly. 

Phase 2: Assess (Days 0 to 30)

This phase is about evaluating current sales team performance, initiatives and structure and how well-aligned these are to new buying realities. It’s also about determining functional priorities to develop your strategic plan. Benchmark sales’ functional maturity and develop a strategic plan that prioritizes pressing external and internal issues along with achieving enterprise goals.

During your first few months, treat each interaction with a direct report as an assessment. Determine whether your current team has the skills or willingness needed to support your vision for sales. This is especially critical now as the consumerization of B2B buying has forced a major reboot in the skills, tools and processes needed to thrive in the current and postpandemic world. This shift has both created a rising enthusiasm for some selling in the new environment and, for others, a revelation that they no longer want to (or can’t) sell in a new, more digital and more virtual commercial environment.  

For your key team members, document any themes or trends you observe from your conversations. This will help you identify professional development areas and uncover untapped potential within your team as well as any sellers who have not adapted with the rest of the world.

Phase 3: Plan (Days 15 to 45)

Use the plan phase to address any identified pressing issues. Integrate the information from the assess phase into an actionable plan for the next one to two quarters and long-term plans for the first six to 12 months.

Ensure that the plan includes quick wins, as this will help you establish credibility quickly. To do this, identify small projects (“low-hanging fruits”) bounded by time and scale that can help you make meaningful improvements to the organization. The best quick wins are collective — executed with the help of your direct reports and even the broader sales community. 

Learn more: 2021 Strategic Roadmap for Sales Leaders

Phase 4: Act (Days 30 to 80) 

This is your opportunity to put plans into action and deliver visible results. Refine your team, get involved in existing projects, execute a quick win and continue communicating your plans to the CEO and/or your manager, as well as other key stakeholders, to establish formalized feedback loops. Watch progress closely to ensure that obstacles to execution are dealt with swiftly and continue your information gathering internally to iterate the longer-term plan.

Phase 5: Measure (Days 45 to 100)

The measure phase is your opportunity to start demonstrating the evidence of your influence. Share metrics, data points and anecdotal feedback showcasing the effect of your initiatives. Identify the parts of the plan that are working well — mentioning early wins and progress — and challenges that need more time or additional resources.

Toward the end of your first 100 days, prepare a short presentation for your CEO and/or manager and team that tells the summarized story of your project outcomes and key findings. Keep your presentation simple; provide a summary of what you learned, potential organizational and process changes, next steps and (most importantly) where you need their help. Then mobilize your clear plan and aggressive timeline — because now you’re ready to move fast.

This article has been updated from the November 2019 original to reflect new events, conditions and research.

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Recommended resources for Gartner clients*:

Recommended Gartner client* reading: The Chief Sales Officer’s First 100 Days

*Note some documents may not be available to all Gartner clients.


*Note that some documents may not be available to all Gartner clients.