Practical Ways Sales Enablement Leaders Are Connecting the Dots to Improve Sales Performance

Growing a business has become a technology enabled, data-driven team sport. This has put sales enablement and operations directors on the front line of the struggle to  “connect the dots” across people, process and technology to generate more scalable and consistent growth.

Much like non-commissioned officers in an army pivoting to face a new threat, enablement and operations leaders are essentially acting as the sergeants, lieutenants and corporals on the front line who put the troops, equipment, ammunition and intelligence in the right places – ideally faster than the enemy.

This is actually good news for enablement professionals. The quest to build a “high octane growth engine” from the many modern selling practices, technologies, methods, and systems within their commercial organization is good for their businesses. It’s good for the revenue teams they support. And it’s good for their career trajectory.

Why now? The reason is the modern commercial model has reached a tipping point. Sales enablement teams are finally in a position to break the back of the historic issues of achieving consistent performance improvement and a material return on technology investment. Enablement leaders have the management support, expanded remit, and a critical mass of systems and tools to finally make a dent in sales productivity numbers that feel like they have been stuck in the mud over the past few decades.

It’s about time. The most recent benchmarks from Salesforce show  in time spent with customers (34% of rep time) and quota attainment (42% of all reps) have a lot of room for improvement. The current environment at most B2B sales organization is much more conducive than ever to move those numbers up. The core systems are in place to finally turn technology into a force multiplier. Today, most B2B organizations have the fundamental CRM, sales enablement, training and engagement platforms in place to materially simplify, augment, and streamline the day-to-day seller experience. Investment in selling technology on a per capita basis is on a path to reach $10,000 per front line seller  as the commercial technology and the “owned” channel infrastructure that supports sales and marketing channels now represent 25% and 35% of operating spend respectively according to the Revenue Operating System report. These investments in systems, training and technologies are far more scalable and productive than the paid media, travel, real estate and other selling overhead they have displaced.

Progress will not come easily. And it won’t happen in one big chunk. Also, it will require enablement leaders to take some new skills and priorities. According to Bob Kelly, the Founder of the Sales Management Association, the keys to driving sales productivity in a modern, ever changing, commercial model include:

  1. Improving the ability of sellers to keep pace with the market;
  2. Making the focus of sales technology improving, streamlining, and simplifying the seller experience;
  3. Improving the timeliness and alignment of your top down and bottom up sales planning processes;
  4. Focusing on incremental process improvements over time rather than large change management initiatives;
  5. Developing management acumen in change leadership.

To carry the military analogy further, enablement leaders on the front lines must make these changes happen in a noisy, fluid and increasingly complex environment. They are having a lot of things thrown at them at once. The technology stack has become more complex with more moving parts.  The customer buying unit has as well.  They are being asked to deploy more content, playbooks, and methodologies and programs than ever before. And align with their peers in marketing, finance, and customer success to support the entire revenue cycle.

So it’s imperative for enablement professionals to focus on the most important programs to invest in and have confidence that the bets they are making will generate business outcomes, according to Michelle Sidwell, the SVP of Enterprise at SalesLoft, whose team has grown sales significantly in the last year.  “Enablement leaders are being asked to simplify the tech stack, change the behaviors of front line sellers, influence the individuals on their team to make those changes happen, and get alignment across leadership so all the different parts of the revenue engine are moving in the same motion,” says Sidwell.

Haley Katsman, the VP of Revenue Strategy, including enablement, at Highspot, reinforces the importance of taking smart, incremental actions to unify the enablement strategy in ways that drive business results. “With so many planning initiatives and programs to manage, it’s important to keep focused on making sure all those efforts are aligned to achieve the growth targets of the business,” says Katsman. “Today’s reps are being asked to do so many things – training, adopting methodologies, changing their behavior – but they really need to know the specific things they need to do to hit their quota. Oftentimes companies’ strategies don’t align with quota-attaining behaviors and programs, and so what reps are being asked to do conflicts with their goals.”  

One key is not trying to take on too much at once. The most successful leaders are embracing the notion of continuous process improvement. They are taking small actions to eliminate the variances in individual process steps, stripping excess capacity and waste from the system, and allocating resources and capability to their most profitable use in creating throughput (sales). They are applying the practice of continuous process improvement long used to optimize production and the supply chain processes to the demand chain processes – meaning marketing, sales and customer success. For example, enablement leaders are starting to use the feedback loops from their training and enablement systems to take a closer look at overall selling team performance — like adoption rates, participation rates and quota attainment across the entire distribution curve. “Leaders need to look beyond focusing their efforts on just the top performers and think more about the frozen middle of the bell curve to find ways to move average performers over to the right hand side of the bell curve from an attainment standpoint,” says Michelle Sidwell.



Another key to creating a highly efficient revenue engine is to focus on making things simpler. This includes simplifying the day to day seller experience and the administration of the systems that support sellers. The key to accelerating sales with technology is (and has always been) giving salespeople simple tools that make it easier to do their jobs and manage the sales pipeline. This makes common sense to any sales rep. But it also makes financial sense. Even an inexpensive sales tool will not pay off if salespeople don’t use it. Having conducted exhaustive evaluations and selection processes at IBM, Red Hat,  Lenovo and Canonical, I’ve learned the key differentiator – and driver of value – always comes down to simplicity, intuitiveness, and user adoption in the eyes of the sales user of process or tool. When it comes to sales technology, you don’t want “BMW Price and Performance” but rather “Apple Elegance and Simplicity. Simplicity contributes to easy and natural user adoption that does not overwhelm sales reps and is sustained over time.”

Another key to success is that the team that “connects the most dots” across the systems, content, methods and tools in the commercial arsenal wins. The technology stack has become so complex – and the need for alignment and teamwork so great – that its far better to have platforms that work well together, than a bunch of best of breed solutions in silos. Enablement leaders are connecting the dots across their technology stacks in ways that simplify the seller workflow, accelerate skill development, support contextual learning in real time, and create feedback loops that support better measurement and ongoing improvement. One immediate area we see this happening is the rapid convergence of sales enablement, sales training, and sales engagement platforms that equip, train, and coach front line sellers. A big underlying reason the sales enablement, training and engagement categories are converging is because they fundamentally support the same selling workflow and run on the same content and data. Over the last decade these capabilities have expanded and overlapped because they support the same fundamental day-to-day selling activities – target, prioritize, prepare, engage, follow up, report, and repeat. These platforms also use the same content – sales plays, training content, product content, methodologies and selling content – to prepare for meetings, practice the skills needed on the call, and communicate with the clients before, during and after calls. And they also increasingly use the same data to run – all three activities are informed by customer engagement and seller activity data.  Much of this data is now drawn from actual presentations and conversations – via zoom call recordings or practice demo presentations by reps.

You can learn more about how your organization can adopt these and other best practices to build your own high-octane revenue growth engine by reading the Tuning The Revenue Growth Engine Report. It will teach you four steps your organization can take to improve the speed, engagement, and productivity of your sellers by over 50% while cutting costs by consolidating, simplifying and optimizing your commercial technology portfolio.

You can learn more about our financially valid blueprint for consolidating, simplifying, and optimizing  the commercial technology portfolio at our CXO NEXT Revenue Operations management forum on September 21st in New York City. At this invitation-only management workshop members of our Revenue Operations community will participate in open discussions about the evolution of sales operations, training, and enablement functions and the integration with analytics and operations teams in marketing, finance and customer success. Operations leaders and managers are welcome to in a peer-led and research-informed discussion of the hottest issues facing RevOps leaders. Topics will include: How to best overcome the challenges of managing change, balancing results with capability building, fostering teamwork along the revenue cycle, prioritizing smart actions, and consolidating the commercial technology portfolio. You and learn more about this forum at the link below.

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