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As more organizations establish sales enablement functions, there’s a rising need for talented practitioners.
Research drives the point home: formalized sales enablement programs significantly outperform those with informal or random strategies, according to CSO Insights, achieving up to 40% better win rates than less-disciplined approaches. And we can safely assume that those high-performing companies have someone leading their sales enablement efforts.
“For sales enablement to make an impact, you need to invest in it,” says Brendan Cournoyer, Brainshark’s VP of Marketing. “That can mean technology, but first, it means people. If you don’t have a full-time enablement person leading the way, success is that much harder.”
Of course, finding the right sales enablement leader can be tricky. There’s no one-size-fits-all definition or skill set for the role. Company size, industry, and sales cycle length can all affect what the ideal candidate looks like, as well.
Crafting a detailed sales enablement job description is an important first step. But you also need a buttoned-up interview process that can determine, in a short amount of time, who is (and isn’t) a good fit for your organization.
Wondering where to start? Here are 7 interview questions to ask when searching for your next sales enablement superstar.
1. Describe the sales enablement program or initiative you’re most proud of. How did you make it successful?
Sure, this is a common line of questioning. But the key for interviewers, according to sales enablement recruiting expert Dave Lichtman, is to understand how candidates have achieved their successes.
“Listen for an underlying problem they were trying to solve and the steps they took with the rollout,” says Lichtman, founder and CEO of Enablematch. “Do they understand the nuanced best practices to execute programs effectively? Do they know how to foolproof their programs to ensure their success?”
2. How did you align sales enablement metrics with company/team goals?
Connecting sales enablement initiatives to the big picture – how are we affecting sales productivity and results? – is critical. But what that looks like depends on the maturity of the company’s sales enablement function, according to CSO Insights. A less mature program might focus on metrics such as time spent selling or searching for content; a more mature organization might directly tie initiatives to sales results (i.e. conversion rate or win rate).
In either case, you’re looking for evidence that candidates could show ROI for programs they executed at previous companies. For example, if revamping sales onboarding was a priority for the interviewee’s last employer, did they demonstrate success by measuring the program’s impact on time productivity for new hires, or training costs?
3. How often do you meet with cross-functional department leads and sales leaders?
Collaboration is a key skill for any sales enablement leader. Use this question to gauge how candidates work with other teams, and follow up by asking what they think is most important to discuss during these type of meetings. You need someone adaptable enough to work with diverse groups – such as marketing, product, and HR – while ensuring everyone is aligned behind a single sales enablement vision.
“[Sales enablement] is the hub that spokes out to every other part of the organization, which kind of makes us the translators of languages and dialects,” says sales enablement consultant Roderick Jefferson. “We have to be able to speak marketing, product marketing, engineering, HR, etc.”
4. Describe a time when you were asked to shift priorities. How did you handle the situation?
Your next sales enablement pro needs to work well with peers, but also with leadership. Listen for plausible examples that show the ability to adapt on the fly, as well as a willingness to engage in healthy debate when needed.
Why? The reality is that nobody – whether they’re the CSO, the CEO, or anyone else – will agree with you 100% of the time. What matters is knowing how well they respond to potential conflict. Do they know when to speak up? Do they have a willingness to fight for their ideas?
5. Have you developed a sales enablement charter? Describe the process/approach.
If you’re hiring for a leadership position, you need someone who can think strategically and gain buy-in from key executives. Creating a sales enablement charter not only checks both boxes, but it’s also associated with 19% higher win rates, according to CSO Insights.
A charter – or a business plan that clearly defines the organization’s vision and goals for sales enablement – should include key details such as services provided (e.g. coaching) and how enablement success will be measured. Look for these elements in your candidates' charter, if they had one.
6. Describe your process for change management.
Change is part of life in sales. Buyers, markets, the competition, the product, the company – none of these things remain the same forever. A great sales enablement leader will know how to encourage sellers to adopt new behaviors as a result of these changes. In fact, you could argue that sales enablement IS change management.
Therefore, you should look for someone who has practical experience driving change. For example, if the candidate’s previous company went through M&A or implemented a new sales methodology, what did the sales enablement plan look like? Did they have a formalized process for communicating changes to reps and their sales managers?
7. Where does sales enablement sit in your organization? Who owns it, and how big is the team?
While there’s no single correct way to structure a sales enablement team, some candidates’ backgrounds might fit your organization better than others’. This question not only gives you a better sense of an applicant’s sales enablement experience, but it also helps you assess how difficult the transition might be if they’re hired.
For instance, a sales enablement “army of one” who reports directly to the CSO might require a different skill set and temperament than someone who works within a large enablement team that sits within sales ops.
Final Note: Probing for Potential Red Flags
On top of asking great questions, you need to conduct the same due diligence you would for any job opening. For example, Lichtman suggests looking for evidence of job-hopping on candidates’ LinkedIn pages. While this isn't necessarily a red flag by itself, it's worth asking for more details if you see several short stints or gaps between jobs.
“People often say VPs of Sales have a short lifespan, but it's also somewhat true for those running sales enablement teams,” Lichtman says. “Look for red flags there and probe deeply into those you find.”
You should also gauge how well candidates manage the little details of the on-site interview, such as sending thank-you notes, researching your company, and asking good questions themselves.
If the interviewee appears disorganized or unprepared in the interview, this person might not be the best choice to lead your sales enablement program. After all, the role demands communication, organization, and multi-tasking skills.