Build an airtight onboarding flow

Humans are great at many things. Knowing what others know is not one of them. For example, try this challenge:

1. Grab a partner
2. Tap the tune to a popular song on the table
3. Have your partner guess the song

What the people tapping often find is that their partner struggles to guess the song. What seems like a simple task isn’t. To the tapper, it’s pretty frustrating. How could they not guess? It’s so easy! But it isn’t, because unlike the tapper, the listener isn’t hearing the song in their head. (This challenge was invented by psychologist and author Robert Cialdini to drive home this point.)

Your onboarding process is similar. We’re lousy at anticipating what others know, so this process exists to provide everyone with the same uniform education. It pulls all those ideas, terms, processes, habits, and conventions into one place for complete coverage. And because your onboarding process lays out a timeline and agenda, it creates a structure that supports learning. People get to learn things in pieces and assemble them in the safety of a role play.

With a thorough onboarding curriculum, it doesn’t matter what preexisting knowledge a salesperson does or doesn’t have. They’ll still know what’s coming, can start to study ahead, and figure out for themselves what all that tapping is about.

Reps should always know what’s next

Joining a new company can be bewildering. All the habits, jargon, and expectations are likely new. For them to absorb and retain information, they need the certainty of knowing what’s next and what’s expected at all times. It helps alleviate the anxiety of wondering if they’re missing a training or should be cold calling. Produce an itinerary for each role, as well as a checklist for their learning goals by each month.

Sales onboarding checklist

For hockey-stick growth, help managers trust and empower their people

As the old adage goes, salespeople are successful due to timing, territory, and talent, in that order. But salespeople aren’t self-sufficient automatons. Most also need to feel valued and supported, and that’s something onboarding can help with.

Design your onboarding process to cover all housekeeping and basics so managers don’t have to worry about that. This frees them to focus on higher-order trainings, shadow on calls, provide corrections, and offer more thoughtful coaching.

It’ll also help managers consider their role as mentor and not player coach. Many sales managers who were themselves formerly quota-carrying salespeople have a difficult time allowing their reps to make mistakes. If they see a salesperson struggling, they’ll feel a near overwhelming urge to save them and close the deal. But they must resist. Salespeople are only going to learn when they get to make mistakes. If your onboarding is thorough, it helps managers relax, step back, and allow the rep to guide more of their own learning.

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You need a precise definition of a good lead and a bad lead

Nothing will create more discord in your sales organization than unclear definitions around what’s a good and bad lead. It’ll cause arguments between SDRs and AEs and between managers and managers. At the VP level, it’ll manifest as missed forecasts and inaccurate data. Everyone needs an objective rubric for answering, “Is this a real deal, yes or no?” or “Does this belong in this stage, yes or no?”

In most organizations, someone leading marketing must define all this, along with the stages in the buyer’s journey, from awareness to repeat customer. But if they haven’t, or things have changed significantly, you’ll have to create your own placeholders. These should become the definitions your marketing operations team encodes into your CRM and marketing automation systems, and what the deal desk uses to make daily judgment calls.

For instance, when someone signs up for a webinar, are they an automatically qualified lead (AQL) or marketing qualified lead (MQL)? Your documentation should specify.

Of course, those definitions may not yet exist. To create your own, look at historical data. Select a cohort of customers and prospects you’d like to have more of and a cohort of customers or prospects you’d like to have fewer of. What actions and characteristics stand out about each? When did the sales team do to win each?

Create a sales cycle definitions doc that includes definitions for:

• A good lead or account
• A bad lead or account
• Stages in the buyer’s journey
• Entry and exit criteria for each stage

“This process is all about defining when buyers enter and exit certain stages to make the sales cycle as crystallized as possible. Whatever you have now, try it out. It’ll be your V1.”
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Rachel Ha'o, Leads Global Sales Enablement at Iterable

30, 60, or 90-day ramp? It’s up to you and sales leadership

Different sales leaders have different philosophies on how long they want reps to ramp, and what they want them to do along the way. Some feel it’s important to expose reps early, having them try and fail in real-world scenarios. Others would rather build their confidence slowly. Either can work. But you’ll need your sales leadership’s complete buy-in.

Milestones in the ramp process:

1. Ramp begins, rep is guaranteed 100% of on-target earnings (OTE) for the ramp period
2. Discovery certification
3. Pitch certification
4. Demo certification
5. Ramp ends, OTE guarantee ends

Ramp assets you’ll need to create:

• Discovery certification—test and scorecard
• Three role plays
• Pitch certification—test and scorecard
• Three role plays
• Demo certification—test and scorecard
• Three role plays

“When a new rep says ‘I’m ready to go, point me in the right direction,’ my response is, ‘Hey, I don’t want you to even send an email for two weeks minimum. Relax, you’re going to be fine.’ I want them to spend those two weeks studying videos of other reps over and over until the pitch feels obvious. Once they’re on quota, if they don’t have the basics down, it’ll be difficult for them to recover.”

Scott Edmonds, CRO at Syncari

In praise of the 30-day ramp

“I have a 90-day ramp for all new reps, but I expect them to do things. I’d like them to close a deal on their first 90 days, and with our sales cycles somewhere between 40 to 60 days, they  need to start taking some calls early. There is a pitch cert and a demo cert, and there is a series of recordings and docs to which they can listen to perfect their pitch. They need to master what’s standard, then develop their own talk track around it. It’s important for everybody to make it their own—it has to come out in their own voice.”

Scott Edmonds, CRO at Syncari

In praise of the 90-day ramp

Hire in cohorts

Whenever hiring more than one rep, time it so everyone starts on the same day. That way, they’re one cohort that onboards together. Much like a class in school. This ensures they’re having the exact same experience and can support each other, rather than having dozens of people all at slightly different stages learning different things.

“The recruiting and sales management teams should strive to hire in cohorts. Get 80% of your new hires to join on the same date. Life happens. It doesn’t always work out that way. The remaining 20% who don’t make it into that cohort are accounted for in that 30-day program. It’s much easier to roll people in on a 30-day cycle than on a 90-day cycle.”

Rachel Ha’o, Global Sales Enablement Lead at Iterable

Don’t allow experienced or enterprise AEs to skip training

Experienced salespeople will often balk at having to onboard. They’ll want to skip. But no matter how experienced they are, they’re coming from a different context and process and if they miss the training, they’re going to be less successful. Insist that they onboard no matter what. The same goes for managers. Just because they’re more senior doesn’t mean they somehow don’t need to learn.

“I don’t fault anyone for this, but enterprise AEs and sales managers-turned individual contributors, they’ll roll their eyes at starting with more rudimentary activities like prospecting or discovery. Tell them, no problem. They can go straight to certification and ‘test out.’ I have never had anyone succeed at that on the first try, and it’s a good reality check. Then they’ll go through the training and find value.”

Rachel Ha’o, Global Sales Enablement Lead at Iterable

Your AE should never fail forward in front of the customer

No matter how experienced or resilient the rep, psychological studies are clear: People do not learn best by repeated public failure. Give your salespeople opportunities to accumulate confidence and competence with graduated exposure to prospects.

“Sometimes sales managers come to me and say, ‘Rachel, we want our new hires to be customer-facing as quickly as possible. They learn faster when they make mistakes in front of the customer, so we don’t want them doing demo certifications anymore. We just want them to demo customers as soon as possible.’ That’s bad for a lot of reasons. One, if you are the AE and you made a mistake on your first customer call, and it’s recorded for all to hear, you’re going to be mentally depleted and your confidence will tank. You’ll be less likely to be successful. Second, the customer’s confidence in your business is shot. And third, that sort of punishment creates bad habits that take time for you to unlearn, which delays time to revenue. I will die on this hill. This creates trauma. Have people complete their certifications.”

Rachel Ha’o, Global Sales Enablement Lead at Iterable

More unassorted advice

• Presume reps know nearly nothing and define all company acronyms or terms of art.
• Give them real at-bats early, but not so early it damages their confidence.
• Make mentorship a prerequisite for promotion.
• Create an #onboarding Slack channel where new reps can review past conversations.
• Have reps record their thoughts, experiences, and feedback to improve the process.