Stephanie Middaugh

Sr. Sales Enablement Manager, Divvy


Stephanie Middaugh is the Sr. Sales Enablement Manager at Divvy, a financial technology startup based out of Lehi, UT. Stephanie has been in Enablement and Sales Operations positions for about 10 years, focusing mainly on Sales Enablement for the past 3 years.

In this in-depth interview, Stephanie discusses onboarding and shares her tips for creating, maintaining, and growing an effective, engaging onboarding program and discusses what can kill your sales onboarding program.


Accelerate: What are your favorite things about the sales onboarding process? 

Stephanie: I studied to be a High School teacher in college, so my favorite thing about onboarding is the teaching process itself. You have a group of excited and hungry new employees that are jazzed about learning everything they can about a company and its processes. In Sales Enablement, you are often one of their first points of contact in the organization and you are able to set the stage and tone for their tenure at the company moving forward. It’s a very exciting and rewarding experience for me. 


Accelerate: What tips do you have for someone who is creating a sales onboarding program for the first time? 

Stephanie: As you begin to build the framework itself, talk to your newest employees and gather what they struggled with the most during their onboarding. Speak with front-line managers to determine what questions they get asked the most by their new hires. Meet with people from each department and gather what, in their opinion, would be most helpful for someone to know within their first 30 days. 

What I have found to be the best format for onboarding new hires begins with understanding the business itself (who we are, what we do, and how we do it) and then move into more role-specific training (BDRs vs. AE’s vs. Sales Managers, etc).

One thing that is vitally important in my opinion is to make sure you keep the onboarding process an iterative one. You should always be looking to improve the experience, so once you build something, don’t write it in stone. Be open to feedback from leadership, managers, and especially your participants going through the program. Gather their feedback not just right after the onboarding, but begin a cadence 30, 60, 90 days later to find out what they wish had been covered within their onboarding experience. 


Accelerate: What elements are an essential part of sales onboarding? 

Stephanie: To me, there are 3 essential parts of a sales onboarding program:

  • Understand the business (what is the value prop of the company, the elevator pitch, and what sets your business apart)
  • Understand the market (where does your company fit and how does it compete in that market? Who are your target personas, departments, and/or verticals?)
  • Understand internal processes + tools (How will they be compensated? How does your company forecast? What is the sales process? What tools are used internally – i.e: CRM, messaging tools, content repositories, forecasting tools, prospecting tools, etc – and what are the best practices for those tools?)


Accelerate: What are some creative ideas you’ve added to your sales onboarding programs? 

Stephanie: One of the things I’m most passionate about is creating a live onboarding experience that is both informative and engaging. A lot of onboarding programs tend to rely heavily on slide decks to convey information or processes, however, I think this actually tends to do a disservice to those attending your training. 

If you can’t fully remove slide-based presentations, at least inject some elements of fun in front of or in-between the presentations. One of my favorite things to do is kick-off either the day or a session with an interactive game or activity. You would be surprised how much of a difference simply getting people out of their seats can have not only on engagement but on retention as well. These activities can serve as an anchor point that the attendees can call back to later-on. For example, attendees might not immediately remember the hand-off process between the Account Executive and the CSM, but they will likely remember the puzzle game I had them work through with their classmates and they can more easily recall the process from that memory.

Even something super simple like creating “get to know you games” to get people up & moving can make a big difference. Have people line up in order based on when their birthdays are. It gets people mingling and breaking the ice with each other, plus it gets the blood flowing and reboots their brains.


Accelerate: What are some tips you have for creating a sales onboarding program that is beneficial to different learning styles?

Stephanie: This is a crucial piece to any training and this is really where my schooling to be a teacher comes into play. Everyone learns differently, that shouldn’t be a surprise to anyone. Some people will learn best from lecture-style teachings, others will learn best from hands-on teachings, and some won’t learn until they are actually in the scenario. You can’t necessarily cater your trainings to meet each learning style, but you can incorporate elements of each to do your best to address each style. 

For example, when setting up my live training I had some slide deck presentations, some whiteboarding sessions, panel discussions, and then hands-on exercises and activities. Something for everyone. 


Accelerate: What are a few things that can kill a sales onboarding program? 

Stephanie: One quick way to kill and onboarding program is to have nothing but lecture-style, slide deck presentations during your live training. The new employees are excited to be at your company, but 8 hours of slides will suck all of the energy out of the room and I can almost guarantee that they won’t retain much information if any at all. 

Outside of the live training piece, another quick way to kill a sales onboarding program is to not provide all of the valuable information your new hires need in order to be successful. If your training doesn’t provide value, word will spread and new hires will hear the water-cooler gossip that your program isn’t worth their time.


Accelerate: How do you help ensure management buy-in of the sales onboarding program? 

Stephanie: The easiest way to ensure management buy-in is with results. If you’re new to the company, pull examples from a previous role to show them what your plan is and how you will make it work at your current company. 

Another way to get manager buy-in is to explain all of the benefits of an onboarding program. The Manager gets to do what they were hired to do, Manage their sales team. You will own the onboarding piece while keeping in constant contact with them as a manager to ensure you are providing their new hires the right training they need in order to hit the ground running and start crushing their quota.


Accelerate: How long do you think an effective sales onboarding program should be? 

Stephanie: This all depends on your particular business. For more transactional sales, onboarding should be relatively short – probably 2-3 weeks, max. For more complicated sales, an onboarding program would easily extend past the 1-month mark to ensure the rep has everything they need to succeed. 

Find out how long the typical ramp time is within your company (ie: how long does it take a rep to make their first deal and/or meet a quota), and then start setting goals for yourself and/or your team to decrease that time. 


Accelerate: What are your thoughts on companies that want to ‘onboard’ new hires in one-week and immediately put them in front of customers the second week? What tips do you have for helping the company see the advantages of a longer sales onboarding program? 

Stephanie: Again, this all depends on your particular business. If you are a transactional business that hires seasoned salespeople, it probably isn’t out of the realm of possibilities to have reps on the phones with some prospects by week 2. Keep in mind though, the reps should be coached and monitored as they ramp to ensure they are providing accurate information and delivering the pitch and/or demo as they should. 

If you’re hiring reps would have never been in a sales role before, it wouldn’t make sense to put them on the phone with a Prospect or Customer until you can fully train them on the processes and methodologies of your business. Get them synced up with a mentor to dry-run their talk tracks and get familiar with the types of conversations and people they will be speaking to. 

There’s a fine line between an onboarding program that is too long and one that is too short and it’s up to the Enablement department to make sure they fully understand their business and what makes their reps truly successful.  


Accelerate: What are your thoughts on pre-hire onboarding (assigning tasks for the new hire before their first day)?   

Stephanie: I’m not a big believer in pre-hire onboarding curriculum. A lot of people will start a new role the Monday after they’ve left their prior company. New hires will have so much going on in order to wrap up their previous position that requiring them to complete pre-hire coursework adds a level of stress that I think can be avoided. 


Accelerate: How do you define if a sales onboarding program is successful?

Stephanie: The definition of success for an onboarding program should be based on the KPI’s you have set for your business. 

Some high-level metrics should include a type of certification, typically a whiteboard, demo, or meeting set certification. You should additionally measure the amount of time before a rep is fully ramped. “Ramped” can be defined differently in each business, but is typically around time to first deal, time to quota met, etc. 


Accelerate: How does sales enablement technology play a part in sales onboarding?

Stephanie: A Learning Management System can help you store, assign, and present content to your new hires in a prescribed and trackable way. Most Enablement tools offer elements of video training, testing, and often video recording and coaching. 

Recently I went through my own Buyers Journey evaluating LMS platforms and there are a lot of options on the market. My advice is to make sure you understand what your organization needs, how your internal customers learn best, and then how you want to create and present software, and then choose the best platform for all of those pieces. It can be really easy to get caught in analysis paralysis when you’re in that process, but make sure you define what you need and zero in on that. 


Accelerate: Is it possible for a company to put together a valuable sales onboarding program without access to a sales enablement platform?  

Stephanie: There are always ways to get around not having a dedicated technology to solve your problem. In my current role, I had to overcome needed a Content Management System, but not having a budget for one. In this situation, I would recommend utilization of the tools that you already have access to. Are you a Microsoft shop? SharePoint might be an option for you. Are you a Google shop? Google Sites could be an option for you. It won’t be as robust or sexy as a true LMS platform, but sometimes you have to make the best of the situation you’re in and leverage the resources you have at your disposal. 


Accelerate: How does coaching, training and sales management play a part in sales onboarding? 

Stephanie: All of these elements should intertwine when you’re building an onboarding program. Sales Management needs to know what’s being taught by Enablement so that there’s isn’t overlap, but instead a seamless transition from Onboarding into doing their everyday job. Management also needs to be included throughout the Coaching piece as well. They need to know where the new hires are when they first come onboard so that the coaching can be based off existing skills and abilities and build from there. 

Enablement and Sales Management should be closely aligned throughout the entire onboarding process to ensure the new hire has a solid foundation with which to build their career at your company. 


Accelerate: What’s your favorite success story about a sales onboarding program you’ve implemented? 

Stephanie: One of the Enablement programs I came into had a live onboarding program piece that consisted of 5, 8 hour days filled with PowerPoint presentations with very little interaction from the new hires. I immediately implemented ‘energizer’ games in order to break up the lull during the days, implemented morning activities and games to set the stage for what they would be learning that day, and began to challenge our presenters to not use PowerPoint and to instead use another method of presentation. This was especially helpful during our Product explanation as our Product Manager replaced his PowerPoint slides with an interactive whiteboarding lesson which new hires got a lot more out of. 

We saw a 13% increase in positive ratings about the overall onboarding program after making these few, seemingly small, changes. 

Accelerate: What do you think the future of sales onboarding is? 

Stephanie: My hope is that the future of onboarding will incorporate more aspects of adult learning best practices. The Enablement function ultimately touches on a wide-range of aspects within a business, but Onboarding boils down to teaching adults new things and if you don’t understand, even at a basic level, how adult brains retain information best your onboardings won’t offer a lot of value.


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