A Blueprint for a Successful First 100 Days as a CSO

Sales leaders who focus on four main activities during their first 100 days 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. 

“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.’”

With the myriad of 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 the organization’s people, processes, politics and priorities. 

The initial “honeymoon” period in sales is shorter than 100 days, but presents a high-leverage time to advance your agenda

“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 on the wrong foot.”

This is true whether you’re a first-time CSO or a seasoned sales executive joining a new organization. For a smooth and successful transition, follow these four steps during your first 100 days: Prepare, connect, assess and act on key transition issues.

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Prepare to lead

As a new 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 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 “honeymoon” period in sales is shorter than 100 days but presents a high-leverage time to advance your agenda. So plan carefully, but rapidly. Realize that as a CSO, you aren’t just responsible for a function; rather, you are an enterprise leader. This can be a big shift for some, but know that successful enterprise leaders are defined by their outcomes:

  • They achieve strong individual leadership performance by reaching their goals and leading their teams to do the same.
  • They show great network leadership outcomes — working with other leaders and their teams to transfer and acquire resources and best practices.

Learn more: First 100 Days: A Guide for New-to-Role Heads of Sales

Build connections

Understand that your success relies on your ability to make strong connections within the organization. Work intentionally to connect with stakeholders from across the enterprise, including marketing, HR, finance and IT — functions critical to the success of the sales leader and the function as a whole. “Gartner research shows that fostering strong relationships increases transition success by almost 50%,” says Boulden.

It is crucial to build relationships with senior stakeholders and cross-functional partners, but CSOs must also build strong teams within sales. A common barrier to building trust is rushing into projects or decisions without involving the team.

If you are too quick to make a change or decision without consulting your colleagues, or at least walking them through your reasoning, you will likely alienate them and lose their trust in a critical stage. But don’t mistake this pragmatic check point for consensus leadership. As the CSO, you don’t have that kind of time.

Read more: Gartner Top CSO Priorities for 2020

Assess to move forward

This phase is about evaluating current sales team performance, initiatives and structure, as well as determining functional priorities to develop your strategic plan. Make benchmarking sales’ functional maturity and developing a strategic plan to address pressing issues and achieve enterprise goals a priority.

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. 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.

After measuring the function’s current maturity and assessing the other factors above, heads of sales must address any identified pressing issues. Use the results of your assessment to prioritize next steps and develop a strategic implementation plan for the program.

Act to deliver quick wins

To hit the ground running, CSOs can start with quick wins. These quick wins can be achieved in small ways that are completely unrelated to commercial outcomes but still build toward their success.

For example, one new-to-role CSO overheard widespread complaints about the extensive amount of sales manager time that was consumed by the demand-forecasting process, only to learn that many products were actually being forecast based on historical data. Tweaks to focus the forecast effort led to better forecasts and reduced the time sales managers spent in a spreadsheet. This small change was a first step in building broad support from the sales leadership team.

The best quick wins are collective — executed with the help of your direct reports and even the broader sales community. Ask yourself if your quick-win opportunity delivers:

  • Value. Is it linked to an urgent, critical business outcome with a clear connection to revenue growth or cost reduction?
  • Cost and feasibility. Is it achievable without substantially distracting the team from their day-to-day work or using new resources?
  • Collective impact. Once achieved, will the entire team feel they have contributed?
  • Learning opportunity. Does it provide you with additional insight into your team members’ strengths, weaknesses, motivations, aspirations and working dynamics?
  • Relationship building. Has it required you to seek guidance and input from your direct reports, peers and manager?

Communicate your strategic priorities and then develop initiatives to act on these priorities. Be sure to measure progress. Toward the end of your first 100 days, prepare a short presentation for your CEO or manager and team that tells the summarized story of your project outcomes and key findings. Maintain the goal of assessing individual performance with an eye toward optimizing your organization for profitable growth. Be sure to track your collective progress with two or three clear, easy-to-measure indicators. 

Keep your presentation simple; provide a summary of what you learned, potential organizational and process changes, and next steps.

Gartner for Sales Leader clients can read more in Chief Sales Officer: First 100 Days.

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