Onboarding Salespeople

Maggie Callahan has led revenue enablement at Convercent and Four Winds Interactive, overseeing training and onboarding for 80+ AEs and SDRs. In this guide, she explains the key components of sales onboarding and how to design a repeatable process.

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Questions covered in this guide

Why is it worth investing in formalizing sales onboarding?

One of the top board-level questions in growth mode is “how fast can we get new reps to quota?” a strong onboarding practice will help reps reach full quota more quickly. When most sales people only stay at any given organization for two years, it’s a complete waste of money for them to take four quarters to be completely onboarded. 

Relying on other sales reps to lead onboarding is not a good idea – having your successful sales people train new reps takes time away from their selling to hit quota. Plus, the best sellers are rarely the best teachers, and may have bad habits you don’t want perpetuated.

When you don’t give new people context, they will not be successful fast you must tell new people what your expectations are and give them a path to success- whether that’s general information about your sales methodology, your market, your buyer persona, or your stage advancement criteria. 

What are the big components that must be included?

Infrastructure knowledge – instill the value of speaking in a customer’s language and driving home a customer’s value proposition.
  • How your customers make money (their business goals)
  • Challenges and risks that your customers struggle with
  • Areas where customers commonly try to cut/manage costs
  • How customers are impacted by market conditions and world events
  • Who the buyer personas are, what each cares about, and the terms they use
Functional knowledge – after sales people understand their customer, teach them about your sales process (all of these things become easier if they understand the customer first):
  • Training on your sales methodology
  • How to write cold emails
  • What to say on a first phone call
  • Good discovery questions to ask
  • How to pitch a quote with value

Experiential knowledge – we start giving reps practical applications early – in the first week we go through effective territory planning and speak with the sales reps about how they’re going to identify the best accounts to pursue and account plan with them. Then, they choose an account to go with them through the remainder of the onboarding process. All of the functional knowledge training can be applied to specific opportunities or accounts. 

How does experienced AE onboarding differ from more junior AE/SDR onboarding?

For AEs, I always prefer to promote SDRs from within the organization, for a few reasons:
  1. They’re less expensive.
  2. When you onboard them, they have no bad habits already created. Most startups think they want to hire the most experienced salespeople in their industry, but in reality, whomever you hire has all of these habits they’ve already adopted.
  3. They already have a base knowledge for how to speak your language and the customers’ language in addition to knowing your product.
  4. They’re less likely to fail or leave. Chorus AI did a study that showed that the failure rate was 6% when promoting internal SDR’s with 16+ months experience. Overall, 26% of SDR’s will fail when promoted to AE, whereas external hires will fail at 41% and take four and a half months to be fully ramped.

When onboarding AEs who are new to the org, train your methodology and track your metrics – make sure your company has a cohesive methodology (usually head of sales picks this). If you don’t have a specific methodology and all of the sales reps are “lone wolves” it will be far more likely that new reps fail. Also check your operating cadence to make sure the sales reps are succeeding based on how you measure success. 

When onboarding new SDRs, use an abridged and VERY experiential training – still talk with them in relation to infrastructural knowledge, but shorten the sales methodology piece because they don’t need to know how to move a prospect through each stage of the sales cycle. They just need to understand how to engage the customer, so we talk more about building customer value. We find that SDR’s straight out of college struggle most with confidence, so we also do a lot of role play practice, cold calling, email mock-ups, and qualification.

How long should onboarding be?  

About a quarter for AEs – it varies, some companies go shorter, but a quarter is common. 

About 3 weeks for SDRs – since you’re mainly focusing on a specific area (prospecting and qualification) for them. 

What does the onboarding timeline look like?

First week – general employee onboarding, infrastructure knowledge training, and territory assignment (by end of the first week, the sales reps will have real accounts in their pipeline).

First month – functional knowledge training, with a certification. Before they’re certified to run their first phone call, reps shadow their leader and participate in mock phone calls with leaders and peers, and start building out their pipeline in Salesforce.

Certification – at the end of the first month, the new rep will sit with the sales director and do a full deal review following our sales methodology, a quote review, and a first phone call. The sales leader will grade the new rep on all of those items.

First quarter – onboarding continues with product trainings and certifications through the first 3-4 months of a rep’s tenure.

How does sales onboarding overlap with general employee onboarding?

It’s best to also put AEs through people operations training – covering executive welcome, message from the CEO, and a message from the head of every department so new hires understand the inner workings of the organization. 

How might AE onboarding be different at a company of 5 reps vs. at a company of 25 reps?

Sales leaders are enablement in young, fast-growing startups – the sales manager should be spending the majority of their time coaching (not still spending all their time selling). If you’re a sales manager who needs help with coaching, then my best suggestion is to delegate and work through people operations for onboarding. Have your people operations interview you and then have them leverage an LMS and upload the information and videos into it. 

Hire an FTE as you get bigger – once you get to a revenue organization of 15-20 sales reps (AEs + SDRs), hire a sales enablement specialist. 

What tools or resources make this easier?  How do you create/use them?

A Learning Management System (LMS) e.g. Lessonly. We use it generally for scaling and any trainings that we run. We record all of our trainings and it allows for us to then test people. Any product updates that come out we update through there for any training across the company.

Sales engagement tools – e.g. Outreach or SalesLoft. to track all of our touchpoints in existing accounts. I leverage it to help our revenue operations leader report on adoption of new systems, effective prospecting, and traction into territories. I also work closely with the business development team for writing new messages and sequences to ensure that we are continuously training on the latest best practices from business development. 

What’s the best way to plan AE starts (e.g. time of year, starting multiple together)?

Running onboarding sessions is intense; it’s better to do it with more people – onboarding takes around 32 hours a week, so we always try to start at least 2 people together. We also have other new people from different parts of the company join in on the first week where we cover infrastructural knowledge since it’s not just about sales people. For the time of year, it doesn’t necessarily matter when you’re hiring as long as you have a year-out capacity plan.

What are the most important pieces to get right?

For an enablement leader, make sure that the sales leadership is on the same page – the sales leadership should be creating the onboarding with you even if that means you are giving them your ideas and best practices and allowing them to say “yes, I’m good with this.” It is so important to get their buy in and to make sure there’s something to hold them accountable for in all of it as well because the sales enablement leader shouldn’t be the only one responsible for somebody’s success. 

For sales managers (at smaller companies), invest in structure the more you try to make it “off the cuff,” the more difficult it’ll be for the new rep to understand what your expectations are and how they’re supposed to manage their day. If the sales rep runs into time management problems, that will be one of the key reasons they aren’t hitting their quota. 

What are common pitfalls?

Don’t do every single part of it – enablement leaders and even sales leaders aren’t the expert on every piece of the sales process. Learn delegation and ask for help. It’s also better when the new person who’s onboarding has different people to listen to, so give them some diversity for who they’re hearing from because it will elevate the efficacy of your training programs.

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