Formalized sales enablement functions are relatively new, and most of today’s practitioners haven’t held the role for very long.
Kara Underwood is a big exception.
Since 1998, Underwood has held sales training and enablement roles at several major software vendors, including Adobe Systems, Hewlett-Packard and ForeSee, where she has a long track record of increasing sales productivity and company revenues.
Now, she’s aiming to continue that success leading global enablement at work management platform provider Wrike, which is preparing to grow its workforce by “several hundred” this year.
“Wrike is growing exponentially,” Underwood says. “I’m excited about the opportunity to help the organization scale, achieve its growth goals and improve the time-to-productivity for new-to-role colleagues.”
Few people know the ins and outs of sales enablement leadership better than Underwood. For the latest Q&A in our ongoing blog series, “Sales Enablement Voices,” she shares best practices for getting started at a new company, improving the onboarding process and shortening time-to-productivity for new hires.
Previous Editions of Sales Enablement Voices:
- How to Be a Sales Enablement ‘Superhero’ [Lisa Mauri Thomas]
- How to Handle a Sales Talent Shortage [Colleen Honan]
- The Keys to Great Collaboration [Roderick Jefferson]
- Advice for Aspiring Sales Enablement Leaders [Sandra Nangeroni]
Improving Time-to-Productivity: Q&A with Wrike’s Kara Underwood
How do you approach the first 100 days in a new enablement role?
I like to leverage best practices I learned during my sales career, like facilitating good discovery with your clients. In this case, it’s an internal client.
You should really understand their challenges, needs, inhibitors and best practices. Make sure you’re tailoring whatever you’re building appropriately, and that you’re checking with your internal client on an ongoing basis to ensure it’s relevant and on-target with their needs.
The other piece is to go in and build the business plan. What’s your holistic plan for the first, second and third years? What are your short- and long-term goals? How will you measure your success? What metrics will be measured?
Agree upon goals and metrics with your executive team so you have a dashboard you can report from on an ongoing basis. That helps you get the requisite investments you need from a people and dollars perspective, so that you can align on expectations and priorities. There’s always more to be done than there are resources.
These are all things you’d do in sales. You’re just applying the best practices in an enablement role.
How do you tailor a sales enablement program to the organization?
I put together a task force of salespeople from varying roles and geographies. I’ll work with managers to nominate people to these task forces, and I’ll rotate members so I don’t burn anyone out.
This will give you feedback on all of the different elements of your program – like learning deliverables and best practices – while you’re building it. You have direct insight coming from the field, and over time, you’re continuing to refine the program based on this feedback.
Then when you launch your program, the task force members are positioned as the ones who built it. It wasn’t built in an ivory tower by a training or a learning organization.
It will come across as more of a grassroots effort, because it’s more about sharing best practices across the organization from folks in the field. For me, that has helped significantly.
How do you structure a sales enablement “task force?”
I’ll look for two nominations from each of the primary roles you’d be building the program for. So it could be an inside sales colleague from EMEA and another from the U.S. It could be two account executives from different geographies. Two sales engineers. Two sales leaders.
When you build a program, there are shared pieces of learning and role-based breakouts. You can work with different roles to identify what the best practices are for each and how the program can improve. What helped them when they were ramping into their new role? What resources have helped them be successful? What did they not have that others could benefit from? You need to have insight from people who have been successful in their roles.
You mention onboarding. Why do so many companies struggle to get new hires productive?
You need to make an investment in outlining which the best practices are going to help them ramp as quickly as possible. You must give guidance if you want to see the needle move on time-to-productivity.
What I’ve seen work is putting fact-based content around sales process, sales tools and the solution into eLearning courses, videos or documentation where people can get that content from Day 1. And you commit to maintaining that content on an ongoing basis because it often changes.
It doesn’t matter what date new reps join; the content is available to them. It also saves time for the subject matter experts if it’s recorded once and maintained with updates vs. spending multiple hours every month delivering the same session.
It’s important to complement the self-paced enablement and shadowing with a workshop where new hires can meet with the experts and ask questions. If you’ve already covered the foundational knowledge up front, the workshop is all about deeper-level content, asking questions of the experts and then applying knowledge in the context of a scenario or case study.
What should a good workshop cover?
A workshop is all about applying knowledge in the context of all the major types of client interactions, in order to simulate the sales process. A lot of people will have sales or sales engineering experience. But they need to learn how to sell in the context of your environment, with your sales process and your solution. They need to understand some of the pitfalls.
If you only have your workshop focused on information delivery, which is typical of a lot of programs out there, you’re probably not going to see the same behavior change or the same time-to-productivity improvements.
The best use of precious face-to-face time is practicing, applying, getting feedback on areas of strength and development, and asking questions of experts, instead of an information push. When it’s death-by-PowerPoint and fact-based content only, you’re typically not going to have more than 10% retention. People learn when they get a chance to apply, and when they understand the context.
For example, you are not just talking about prospecting. You are asking them to practice writing to a decision-maker that they don’t know. You’re asking them to practice making an outbound call to a new decision-maker. You’re asking them to practice facilitating a business discovery meeting.
How do you typically measure onboarding success?
It varies depending on the company and the role. Time to ramp quota – a smaller quota you’re given during your first couple of months – or time to first deal closed are two of the very popular ones out there. But there are definitely things to consider for each role.
For an inside sales rep, it could be time to holding their first meeting over the phone. For a sales engineer, it could be time to first autonomous demo, or time to facilitating technical discovery on their own. You can also look at the close ratio by salesperson, and the time it takes to get opportunities to a specific place in the sales process.
How do you balance ramping new hires with ongoing learning?
You need a strategy for both. The solution, the process and the tools change all the time. You’re only going to get to a certain level of knowledge and productivity with the new hires. You’ve got to look at how to take it to the next level, keep people up-to-date and continue to invest in them.
I’ve found it helpful to have a regular cadence. You might have a global field call with your tenured folks and continue to share success stories. Examine why you won the opportunity and what were the lessons learned. People benefit significantly from highlighting one of those every time. Having different cross-functional groups present and provide updates is helpful.
You can also use tools like Brainshark to update existing folks on changes. You send out updates and say, in the solution overview course, please review slides 5-10 or review the last module of this curriculum – wherever there were updates made to it.
How do you determine what content needs updating?
The basics are keeping your tools, solution and sales process content up to date. I set up a regular cadence of quarterly meetings with cross-functional groups, and monthly meetings with marketing to check in on the content that is used in the enablement program – and determine what updates or edits are needed. It’s important to have a maintenance strategy for your program.
The other piece is addressing inhibitors and challenges in sales process for tenured folks. Is it a lack of profitable deals, which means negotiation needs to be an area of focus? Is it that you need to sell to a higher-level decision-maker, because you’re currently selling more to the functional or technical buyer? Do you need to focus on business acumen and building business cases with metrics?
A lot of people rely on instructor-led programs only. However, those take a lot of subject matter experts to facilitate and dollars to keep delivering the same content over and over again. If you put that content online, then you only have to update the pieces of it that have changed.
That allows you to reduce the amount of time in face-to-face workshops and spend precious in-person time on interactive discussions and skills practice exercises based on simulation.
What’s one tool you use to improve your own productivity?
I probably would go with Wrike. It’s a work management and collaboration app that allows you to manage several different projects and programs effectively. You can collaborate with dispersed teams, keep track of progress for key milestones and communicate with a cross-functional team effectively. It’s very user-friendly. Especially as a learning person, Wrike can make day-to-day work easier and more efficient. It’s a tool that I’ve seen the value in personally.
Download our exclusive eBook to learn how a fresh approach to onboarding can get your new hires ready faster.