September 2018
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Inside the Minds of Chief Sales Officers

Friday, August 31, 2018
Inside the Minds of Chief Sales Officers

Sales enablement's ability to understand the CSO's priorities and goals can cultivate a strong partnership for success.

Chief sales officers are an interesting breed of ego, paranoia, stubbornness, and street savvy. Typically rising through the sales ranks, they've had to hit a sales target their entire life. And as they've grown in their career, the pressure also has grown. Unlike many of their C-suite peers, the concept of performance is simple: Make the number. Period.


The pressure comes from all sides and never stops: Weekly, monthly, and quarterly performance are always under scrutiny. Because the sales engine is so complex, CSOs spend their days bouncing from issue to issue, such as making sure the entire sales team is staffed, having a highly accurate forecast, ensuring the pipeline is consistently being replenished, participating in various corporate initiatives, handling deal escalations, and taking political heat for the company's entire revenue stream.

All the while, CEOs are pounding on them to control costs, reduce customer churn, and improve customer satisfaction. And don't forget the challenge of communicating the realities of the field to the boardroom—in words board members understand.

No wonder it's hard to get time to talk about sales enablement. Yet the sales enablement leader job is one of the most important on the sales team. Done right, this role can offer valuable leverage to CSOs as they work to hit the number.

CSOs are consumed with the urgent and important—endless meetings focused on near-term pipeline, forecast, and escalations issues. Add field visits with customers and sales teams to the mix, and their calendars are overloaded. In the end, little time or attention is left for sales enablement.

Getting on the same page

So, what's a sales enablement leader supposed to do?

It begins by getting inside CSOs' minds. What are their strategic priorities? What commitments have they made to the CEO? What sales performance gaps are they most concerned about? It's also important to understand CSOs' preconceived ideas (and biases) about sales enablement—what experiences have they had with it in their past roles?

CSOs often are new to the organization, brought in to be a change agent. Likely, they view sales enablement as simply sales training. In fact, the word enablement can be vague or even confusing. As a result, sales enablement frequently drops to the bottom of CSOs' priority lists, and they may constantly reschedule meetings. Any face time the enablement leader does get with a CSO may be brief hallway connections, such as "We need to focus on value selling," "Our reps are struggling; we need more training."

Making sure the CSO knows what sales enablement is and what it can be seems like a logical first step. For the CSO to truly understand sales enablement, there needs to be alignment. Sales enablement must be defined and communicated in a way that directly maps to the CSO's agenda. I've seen many impressive sales enablement overview decks and strategic plans—but, too many times, these documents don't resonate with the CSO. Often this comes down to a disconnect in language, framing, and focus.

Let's face the facts: The CSO is almost myopically focused on improving sales productivity in the form of three key metrics: win rate, average sales price, and sales cycle length. Those are the metrics CSOs live by. The time horizon is always short—this quarter or even this month.

In contrast, the sales enablement team uses terms such as programs and initiatives, or worse, its efforts are framed in traditional HR or training language. To many CSOs, it's not clear what competencies or blended learning have to do with hitting the quarter's sales target. When outcomes are defined for sales enablement activities, they can seem vague and time horizons too long term.

Even a sales enablement team's best efforts can damage its reputation with the CSO. Consider the times when departments, such as marketing, ask the sales enablement team to roll out new content. Without proper alignment to the key sales performance metrics, these actions can look to the field like distractions. The sales team's frustration over this perceived noise quickly rises to the top. The negative feedback reinforces the CSO's worst biases. Perception becomes reality, and the sales enablement team appears totally out of sync with the CSO's priorities.

Building a true partnership

Creating a successful partnership with the CSO requires directly mapping the sales enablement activities to the CSO's sales productivity objectives. It starts with understanding where the enablement function is in its maturity. Every sales enablement team is at a unique point in its own development and sophistication. The challenge of aligning with the CSO's agenda is different depending on the function's maturity.

The Sales Enablement Maturity Curve has four levels.

Level 1: Ad hoc. These sales enablement teams have a narrow focus on episodic training execution. Primarily this training is delivered on demand, typically centered on product. There is no systematic, systemic, or proactive approach to field enablement.

In this model, there can be a big disconnect between sales management and sales enablement. The organization views sales enablement as "Can you help with this?" The CSO may say things such as, "What do you mean when you say ‘sales enablement'?"

Level 2: Tactical. At this level, basic sales training and onboarding programs are in place and they just run. There's probably a major emphasis on events, especially sales kickoff meetings. Sales operations, marketing, or other functions likely dump requests on the sales enablement team to fix problems.

In this model, the CSO isn't thinking about sales enablement until something is broken or doesn't appear to run well. Sales enablement is simply a part of the sales management infrastructure, seen as an executional support resource. The most common thing heard from the CSO may be, "What's the agenda for the sales kickoff?"

Level 3: Integrated. Sales enablement programs are integrated and connected to a common methodology. There is a clear mapping between programs and the overall sales strategy. The team takes a dual focus on improving both sales representative and sales manager performance. Product, marketing, and sales work together to put the right content at the right time in the hands of the right people.

In this model, leadership sees sales enablement as the go-to resource. At this level, the CSO likely says things such as, "Can we meet to talk about my initiatives for next quarter?"


Level 4: Strategic. Sales enablement at the strategic level is unique. Beyond training, messaging, or process experts, a strategic sales enablement team will include additional capabilities in the form of performance consulting. These resources leverage data to make informed recommendations to increase sales productivity.

In this model, the strategic sales enablement team sees its mission as implementing the corporate strategy through the sales team. The sales enablement function has a pulse on the field, constantly assessing gaps and tailoring programs to improve performance. It leads the conversation with the CSO versus being seen as a service function. You know the sales enablement team operates at this level when the CSO is heard saying things such as, "Can I get an update on where we are focused for the next quarter?"

Moving toward alignment

Evolving from order-taker to sales performance consultant is the key to aligning the sales enablement team with the CSO. Unfortunately, most sales enablement teams are at the early stages of their maturity. The shift toward performance consulting doesn't happen overnight and not without a plan.

Think about the significant difference in staff capabilities between Maturity Curve levels 1-3 and level 4. Performance consultants evaluate the current sales situation through the lens of commercial awareness. They are comfortable with data and can build the required solutions. Even more importantly, they can build the case for change with senior leaders by defining the business impact for any new enablement program. Finally, true sales performance consultants track success and measure the impact of their programs using the metrics CSOs care about.

Advancing through the Sales Enablement Maturity Curve also means a focus on improving the sales team's situational adaptability. Levels 1-3 sales enablement teams tend to prioritize core selling skills and the basic sales process. The fundamentals are important, but at the strategic level 4, the sales enablement team delivers programs to help reps assess, prioritize, and adapt to different selling scenarios. Through strong deal situational awareness, reps and managers identify the critical opportunity factors and patterns. They then execute the right sales action or play to match a particular situation. During a complex deal, enablement tools and support help reps pivot the selling tactics to fit the moment.

When the sales enablement team operates at level 4, CSOs (and CEOs) pay attention. The linkage to the metrics they care about is obvious and the impact direct and meaningful. In fact, we've seen high-performing sales enablement programs drive 18-point increases in win rates, not to mention tangible gains in deal size and sales cycle lengths.

Winning the CSO's heart and mind

CSOs have a tough job, but so does the sales enablement function. Too many times, sales enablement teams make their jobs more difficult when they use the wrong language or when they don't frame their work in ways the CSOs can understand. To strengthen the perception and performance of sales enablement:

  • Appreciate your CSO's daily pressures and understand his strategic agenda.
  • Link your program or initiative to your CSO's key sales productivity metrics.
  • Assess your current position on the Sales Enablement Maturity Curve. Build a road map to move forward. Communicate that plan to the CSO.
  • Review the capabilities of your sales enablement team. Make a plan to boost performance consulting capabilities, including skills in data analytics.
  • Lock down the fundamentals. Also, design a strategy to expand the sales team's adaptability. This approach must address ways to increase sales representatives' situational awareness as well as tailored sales plays that fit common deal scenarios.

The CSO is more than your internal customer. Simply being service-oriented and responsive to a CSO's requests isn't enough to build the strong partnership she needs and expects. Likewise, getting to know what a CSO wants is more than just asking. Understanding what the sales organization needs, even over and above what your CSO wants, leads to success.

The path to a high-performing sales enablement function can be difficult. You'll need the CSO's full support just as she needs your support to make the number. But the effort to build a strong partnership between the sales enablement team and the CSO is well worth it—to the sales enablement function, the CSO, and the broader organization.

About the Author

Dan Perry is a partner of the Brevet Group, a sales consulting firm.

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