Building an Onboarding Plan that Scales

Sam Merlo
6 min readJan 3, 2022

Projecting huge growth in 2022?

How will you onboard all your new sales reps?

If you are onboarding every month like I have, you'll find it challenging to juggle the needs of your current team and new hires.

Here are 9 tips to building an effective, fast onboarding plan:

Automate Repetition with Short Videos

Try to automate wherever you find yourself repeating the same information with each new rep. Videos work great for this — but rely on short, bite-sized videos. That way, your rep can more easily absorb the information and rewatch the video when necessary. These work great for training on tools—for example, Salesforce. Don't create an entire video about SFDC; create something 1–3 minutes long describing how to create an account or open an opportunity. Build these videos out into a learning path using a tool like Udemy.

Give Handouts

These are short go-to guides your reps can access when they have questions. Think of them as pre-written notes; they don't replace the notes your reps should take, but they offer reading and reference material. You should have a handout for your qualification questions and maybe one with the step-by-step process for creating an opportunity. You might also offer a "Cold Call Cheat Sheet" or a list of helpful talking points and pitches. Handouts pair well with videos as people have different learning styles, and everyone needs review sessions to learn. You can organize these into a single guidebook or keep them as separate documents. Don't feel the need to make them elaborate — simple is better.

Run Assessments

Be sure to test your reps along the way — but don't make it a judgment session. Just evaluate where your rep is at and what gaps need to be covered. Everyone learns at different speeds. Some people might find it easy to manage SFDC tasks but struggle to articulate a pitch, while others will find the opposite true. You can use simple tools like Google Forms to test, with Udemy you can create quizzes after videos or sections, but some of the best results come when you sit with your reps and quiz them 1–1. Ask them to walk you through the entire process of booking a demo starting with, "Okay, I'm the prospect and I've just agreed to a demo, now what?"

Task a Mini-Project

Break the big picture down into a smaller, specific activity. You can combine this with a co-working session to help answer questions on-demand and build confidence. For example, your SDRs might have to call Flakes in their regular day-to-day — people who booked a demo but never showed up. This task likely involves reviewing qualification notes, using your Sales Platform, like SalesLoft or Outreach, to make and log calls, and creating new demo appointments. Use a report to pull a focused list of Flakes and have your new reps practice the processes and tools they've been learning while also helping out their team.

Tackle Common Concerns

Proactively address common concerns. If you're onboarding people every month, you'll repeat conversations. Get ahead of them. With new SDRs, cold calling prospects will be intimidating — often, it's the most intimidating part of the job. I get in front of these concerns by building skills and confidence exercises into my onboarding plan. New SDRs get a Cold Call 101 training video, a Cold Call Cheat Sheet with helpful phrases and questions sectioned into the "parts" of a conversation, and lots of short Mock Call practice. Also, they get call recordings. I offer two lists for recordings — a few hand selected calls that are great or showcase common problems, and a report which lists recent calls in their region/language. Generally, I narrow the report down to show only calls where a demo was scheduled, where there was interest but the prospect needs more time, or where there was no interest. The point is, give your rep tools for success and a feel for how calls flow. Proactively overcoming concerns is about building both confidence and skill.

Set Expectations

Make sure you schedule a dedicated session to learn what your new rep's expectations are from you, the team, and the role. Learn about their goals and why they matter to them. And, take this time to set your expectations and make sure the rep understands and is aligned with you. Tell them you expect if they want a promotion they have to fulfill their job and go above and beyond. Describe what success looks like. Express your hope that they will connect with the team and make close relationships. If you're hiring junior reps, tell them you expect them to be online during working hours. Nothing is too basic here. You'll be able to refer to this session later if you have to have a pep talk or address performance issues.

That is the "business side" of onboarding — let's take care of the personal side too — your reps are people, after all:

Connect Peers

A happy team is a productive team, and a happy team is created when people like working with their peers. Team collaboration and bonding are crucial to creating a culture of support and mutual progression; especially in a work-remote-world. Be proactive in helping create this. During training, schedule time for your new Reps to meet team members in 1–1s and small groups. These can and should have a goal — such as shadowing morning activities, answering questions, etc. But, you can also schedule free time — time to hang out and chat or play a game. Connecting peers builds relationships, and it offers new hires a way to ask questions without going directly to you.

Encouragement

If you're putting all your effort into building skills, you're missing a crucial element — confidence. Onboarding is as much about encouragement and reiterating your confidence as it is about teaching your new hire "the ropes." Make sure you're taking time to congratulate progress, state your confidence in their future success, and acknowledge hurdles — even if they haven't appeared yet.

Track Milestones

My last piece of advice is to keep it going — don't drop off onboarding after the first two weeks or first month and let your rep out in the wild alone. Create a plan that helps them feel a sense of accomplishment and progression. Explain that it takes time to reach full productivity and help set this expectation with a 30–60–90 day onboarding plan. If you only rely on quota attainment as a measure of success for onboarding, you'll create an atmosphere of fear, uncertainty, and insecurity. Pair quota with other achievable milestones. Each of my reps gets the "ramp up" talk, "Everyone in sales, no matter how experienced, needs time to ramp up whenever they start a new role. This is about pipeline creation and sales readiness — articulating our solution's value in a way our unique audience understands…" Additionally we have hard milestones. At 60 days there is a Pain Points Quiz and Cold Call SAT. At 90 days we have a look back session at progress and set goals for the next quarter.

Learn more about building a sales engine in "Outbound Sales Demystified: Generate Leads and Close Deals." Available on Amazon in paperback & ebook

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Sam Merlo

Sales Enablement Champion for Early Stage B2B Startups