Is Sales Ops the New Sisyphus?

In the Greek myth, Sisyphus was condemned to an infinite loop of pushing a giant boulder up a steep hill, only to have it roll back down again. When it comes to participating in the annual strategic planning process, those of us in the sales ops field can relate. Too often, the strategic considerations we have so carefully raised to leadership end up at the bottom of the priorities list.

As an example, the CSO Insights 2017 World-Class Sales Practices Study asked sales leaders to identify the top issue or challenge they faced over the previous 12 months. Overwhelmingly, their #1 answer was “transforming my sales organization.”

When asked how they translate that challenge into strategies, their top 3 answers were:

  1. Improve value messaging
  2. Improve sales skills
  3. Hire more salespeople


The lowest-ranked answers were “Implement more technology” followed by “Improve sales tools.”

We see this play out in operations on a consistent basis. Sales leaders verbalize long-term strategic considerations like sales transformation, but when it comes down to execution, they gravitate towards short-term initiatives.

The Annual Planning Paradox

The paradox that is constraining sales operations leaders from serving as a strategic partner to the organization looks like this:

  1. At the beginning of the year, executives and sales leadership refine their go-to-market strategy. From this strategy, a “sales execution plan” is developed for the year.
  2. That sales execution plan is targeted exclusively towards meeting and exceeding that year’s revenue goals.
  3. Once this is ready, sales operations (and sales enablement) go through an exercise of developing a support plan which could include looking at new tools or technologies or defining new processes or protocols but only if the sales leader is convinced that the benefit of those investments occurs inside the current fiscal year.


The paradox is that sales leadership is required to think in terms of an annual cycle of revenue performance. But, sales operations has to think in terms of multi-year investments in technology, tool sets, and even processes.

The solution to the paradox is to first assess long-term investment options and develop a plan from there. Here are three suggestions for helping your organization do that:

  1. Help them recognize the problem

If your organization doesn’t have a specific opportunity to assess long-term investment options for the salesforce that transcends the fiscal year, then your organization is missing an opportunity to innovate.

The sales operations team should have a segment of time to present innovative, long-term ideas during the development of the latest sales execution plan. This presentation should include, at a minimum, a traditional SWOT analysis of the potential capabilities and limitations in the current technology stack, guidance on emerging technology or tool trends, and recommendations for a long-term plan. (Many of these recommendations will be very un-exciting data management and control requirements, but that’s the nature of technology and process management).

If you can illustrate how not making these investments could harm their in-year revenue attainment goals and limit long-term growth, you will capture their attention.

  1. Create a sales effectiveness council

If breaking into the sales execution planning session isn’t a possibility, then the next option is to create a “tiger team” focused on seller effectiveness. The purpose of this “council” is to address the long-term ramifications of any investment in tools, training or technology. But it doesn’t have to start as a formal, decision-making body; you can use the council as a mechanism to introduce emerging technology trends or innovative ideas for them to consider, and allow the “authority” of the council to grow organically.

  1. Bring Your Analytical “A” Game

When you are ready to communicate your long-term recommendations, it is imperative to provide benchmarks in order to confirm the current productivity of your sellers. Include time-based analysis showing how much selling time your sellers have, and metrics illustrating critical activity-based KPI’s like number of proposals, lead conversions, average win rates, etc. And, of course, you should have revenue performance benchmarks per seller role. The key is to demonstrate how much productivity you are currently driving through the sales organization, and you should be able to gauge improvement in future quarters or years based on the investments that you make.

If you want to be a strategic partner to your organization, you have to elevate your point of view to the same level as your executives. Ask yourself: Do we have the right organizational structure and decision-making alignment across the company? Do we have the best mechanisms for the long-term success of our company in place? Thinking about these questions from the point of view of sales operations is important to your company, and communicating your concerns is the only way your organization will address them.

No Comments

Post A Comment