Kieran Smith
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Kieran Smith manages GTM Enablement and Productivity of the EMEA & APAC regions at StaffBase. They provide a central, simple, user-friendly platform for company communicators and employees with the goal of establishing community and shared purpose at work.

In the interview, Kieran talks about the flip side of overhiring sales reps to drive revenue growth and suggests more efficient ways to boost sales productivity.

(‍This conversation has been edited for length and clarity.)

Enablement and the C-Suite

If the enablement function wants to make a difference, individually or as a team, we must be part of early conversations with leadership as early as possible. This will equip enablement with the required understanding of the business and help gain respect from the C-suite.

At my last company, enablement was reporting directly to the CRO and everything we did was tied to the objectives and strategic initiatives of the overall business. 

The enablement department needs to be empowered to ask, “Why are we doing this? What is the impact this will have?” This requires the full support and backing from the CRO or the leadership. Nobody has time right now to work on things that won’t make an impact or move the needle.

Empower your teams to ask, ‘Why?’
Empower your teams to ask, ‘Why?’

Best practices for tough times

Enablement works best as internal consultants bringing a unique perspective that connects marketing, sales, and customer success.

1. Instead of overhiring, focus on enabling your existing sellers

Companies have tried to drive revenue growth by hiring more people, especially in the last five to ten years. They simply thought, “We need another million dollars ARR, which means the target is roughly 200 per rep. So, we’ll hire five more reps.” 

However, hiring more sellers may be the longest, most expensive way to revenue growth. And the most ineffective in terms of ROI. 

Even if we onboard people perfectly, they’ll still take time to get up to speed, and many will still leave the company. We have seen massive churn and layoffs because of this strategy, especially since last year.

Today, hundreds of thousands are being laid off because companies over-hired personnel without looking at productivity rates, capacity rates, or other relevant metrics.

Enablers are in a fortunate position not to be tied to the number. However, as enablers, we need to step back and objectively evaluate where we are now and where we want to be - and the requisite skills and competencies we need to get there.


Enablement should be there to help with the talent already in the room, rather than hiring more sellers.

2. Think beyond onboarding

In many organizations, enablement is considered to responsible for just onboarding new reps. You can see this in job descriptions for roles in sales enablement managers. 

This is an antiquated way to look at enablement. While important, onboarding is just part of what enablers are responsible for. If you are in an enablement team that works only on onboarding, you are working reactively and will be relegated to a support function. You will be seen as a cost center because you are not being proactive or leading with impact.

You may be training new reps on objection handling as part of onboarding. However, objection handling is only a lagging indicator. Even if a rep gets better at objection handling, it may not help move the needle at all.

3. Track the right metrics

ROI is multifaceted. 

For instance, if we roll out a new sales methodology, we will look at adoption rates and other metrics. The adoption rate will provide clarity into revenue and also feed into the performance or productivity of a region, team, or individuals. Ultimately, these are the metrics that enablement has to start with. 

Enablement may not own outcomes but it can help influence them by driving behavior change or upskilling people to do the right thing. 

But everything has to tie back to revenue eventually, either directly or by driving the adoption of a sales methodology that helps improve performance. 

However, that is a very shallow metric compared to where we can dive deeper.

The thing with enablement influencing outcomes is we always want to focus on and track the outcomes. But, there are several other components. For example, enablement as a function disappears without frontline sales leaders being bought in and consistently reinforcing what we are doing.

Turning invisible!
Turning invisible!

Everyone in the organization is accountable for the overall performance. When considering ROI, we could look at metrics like sales velocity. 

Suppose the goal is to increase the number of opportunities by 10%. While that is a high number, we have to work backwards from the goal. What are the competencies required there? Which teams? Which regions? How do we go about it? Here is where we need to get creative.

Be clear on the following: 

  1. What will the ROI be?
  2. What is the benchmark prior to starting? 
  3. Where do we want the ROI to go?
  4. What is the time period? (It is easy enough to say 10% overall improvement, but is it over one quarter, two quarters, or the year?
  5. How will we track success and what are our milestones? 

We have to dig deep and understand what we are looking for regarding ROI and impact.

4. Take a proactive approach to enablement

If I had to choose a single tool/technology for driving enablement, it would be conversational intelligence. 

Conversational intelligence gives us an understanding of what is actually being said and done in the field. These insights can help make enablement proactive, data-driven, and bespoke. 

Let us take scorecards as an example.

In my previous organization, we had scorecards by role. We had one for cold calling for SDRs and another for discovery or qualification for AEs. We broke it down by the competencies we wanted to see, such as setting an agenda. 

We asked managers to score one scorecard per rep per week. Sometimes we would get more, but over the first six to 12 weeks, we would get an understanding of every individual by team.

Instead of randomly saying, “Everyone needs training on this,” we would know where individual reps were. Out of an overall score of five, suppose they have a four out of five for relevant, insightful discovery questions but a two for getting a real need or pain point. We now know where to work with that rep specifically. 

There is nothing that reps dislike more than going into a training session that has nothing to do with them. 

For instance, objection handling based on the scores is the most common across all teams. We might have a group of three or four reps who need to work on establishing a need and a pain point. We can work with them specifically and track their progress. Then we can go macro. For instance, when rolling out new messaging, we can look at how many times someone has mentioned this product. We might have to do a catchall with the whole revenue organization with the new messaging. 

After that, break it down and put the data in the middle. 

Be proactive and data-driven. Transparency around data allows us to understand where to look, why we were doing it, and how we would approach it - for both big groups and individual reps. 

Upskilling reps today

Sales is not binary. It is a nuanced profession. However, sales enablement must work to maintain reps at a minimum standard. 

For instance, you might have extra criteria at each stage as your reps move through them. If you look at your CRM, most people have four or five stages, and some even have 10 stages going through a deal. What are your extra criteria? 

Ensure there is a company-wide standard and that everyone understands what they are, whether it is a standard of information or how to close deals. 

Upskilling reps today boils down to understanding and breaking down each stage of the deal. What are the skills required at each stage? 

Sometimes, reps get halfway through the sales process, fall out, and wonder why. How do we run a discovery call? How is that different from a demo? 

Qualified deals mean different things in different companies. In some cases, deals while deals are qualified, there won't be a distinct need or pain point from the prospect. So, enablement has to go back and reinforce that with the reps. 

If you are in a business where managers are now being asked to go onto as many calls as possible to stop deals from falling through, you need to have a separate conversation with frontline managers, the CRO, and enablement about who is responsible for what. 

Handholding your reps forever will not upscale your team

If a director or a CRO is on the call, the rep will be on their best behavior and follow the script. 

CROs want their managers on calls because they bring their experience and skillsets. They have not only been a top performer; they know how to close deals. Does it mean frontline managers should remove the coaching and listening because they were there?

If managers are always on the call, does enablement not have to listen to the calls after? Are the managers debriefing and giving feedback afterward on the realignment required? What about the calls the reps are doing by themselves? 

The way forward

An ideal situation would be when the sales or frontline managers are brought into the same objectives and initiatives that enablement is working toward. Managers can also have coaching sessions, pipeline reviews, etc., where they are asking reps questions. 

For instance, enablement asks a sales rep about a prospect’s pain points. Why does the prospect need to buy this product? However, if the manager is not asking the same thing in pipeline reviews, it will just go out of the rep’s head because it is not being reinforced. This could happen across several areas. 

While it is enablement’s role to enable reps, it is always a company-wide or cross-team responsibility. We have to be on it together, with the leadership, to make an impact.

Feel free to tune in to this interview on Spotify or Apple Podcasts. If you prefer other platforms, simply click here to explore more options. Happy listening!

About the author


Kieran Smith

Kieran Smith manages GTM Enablement and Productivity of the EMEA & APAC regions at StaffBase.

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