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How to Successfully Transition into a New Sales Enablement Role: Q&A with Jill Guardia

Sep 25th, 2017


Starting a new job is no easy feat. Between learning about your new responsibilities, getting to know your new colleagues, and familiarizing yourself with existing processes and systems, there’s a lot to adjust to. Starting a new sales enablement role is no different, and in some cases, it can be even more of a challenge. Sales enablement is still an emerging field, and with each day that passes, the function is continually fine-tuned and modified.

To hone in on the keys to success in a new sales enablement role, we turned to Jill Guardia, a seasoned sales enablement leader, and the Boston chapter president of the Sales Enablement Society – who recently began a new role as executive director of sales enablement at TriNet.

We asked Jill for some advice on what sales enablement professionals in new roles can do to make an impact and the goals they should be setting for themselves.

As a sales enablement leader, how do you set up your first 90 days? What do you seek to accomplish?

JG: My advice for anyone starting their first 90 days is to follow the same path a new sales person would follow. First, do all your e-learning or onboarding pre-work training, attend new hire boot camp, and meet with the sales team. This is important because throughout your tenure you’ll want to put yourself in the shoes of a sales person as much as possible.

Interview as many people as you can. This includes team members both inside and outside of the sales team, as well as company leaders and stakeholders. The first 90 days are your chance to ask any and all questions and learn, learn, learn. Be a sponge, observe as much as you can, and don’t try to change everything to be your way. This is especially true if you are joining a company where there is already a sales enablement function in place.

Keep an open mind that some processes are working, and probably working well. Stay true to your goal of learning, observing, and questioning without opinion. This approach should help you prepare your strategy.

About halfway through your first 90 days, you should be able to test some theories. Experiment with ideas, concepts, and do A/B tests, and see what might stick given the culture at your organization. For example, if we do all of our onboarding online, what kind of impact will it have 6 months or a year from now? Keep your eye on small wins or changes, and see what works. This will give you more credibility to make the long-haul decisions.

What do you look to learn from your sales organization?

JG: In the first 90 days, I’d encourage a new sales enablement leader to understand how the sales process works at their new company. There may be already be a documented process and methodology – but is it followed or is sales success based on tribal knowledge and experience?

Learn about the culture. How do sales happen? Who is selling, and who is closing? Who is the persona(s) you are selling to? Take this as an opportunity to dig into the tools and resources that the sales team uses, how they are using them, as well as which metrics are being captured. All of this, which includes time in the field, will help you understand where the strengths and weaknesses lie, as well as any roadblocks to sales success.

Here are some key questions you should find the answers to in your first 90 days on the job:

  • What does the onboarding process look like?
  • What does the hiring process look like?
  • What is the success profile of a rep?
  • How does your organization determine when a rep is fully ramped up?
  • What kind of activities do you expect from a salesperson in each of the different sales roles? How many calls, connects, or meetings?
  • What are the defined outcomes from each meeting or conversation?
  • Does the sales organization use scripts? Is there clarity within the organization of what a good sales conversation sounds like or is it just understood through tribal knowledge?
  • What does the sales conversation sound like and who is doing it well?
  • What is turnover like and why do people leave? 

What are your tips for seamlessly enacting change?

JG: The best advice I can give here is to first establish credibility. Be in the field, on the phones, listen and offer some tips and coaching help.

In addition, find a sponsor to support you and your recommended changes. Test your changes, recommendations, methods, and programs with a respected sales manager and his or her team.

Lastly, put measurements in place so you can assess the success of your program and then communicate those successes to leadership. For example, try measuring new hire activity from class to class to build a benchmark. Or pick a team and work closely with that manager on coaching techniques and then measure the impact on conversion.

In the market for sales readiness technology to help you achieve success in your new sales enablement role? Download the Sales Readiness Technology Buyer’s Guide to learn more about the most important features to consider.