Million-dollar onboarding questions answered, with Amanda Dossey

Million-dollar onboarding questions answered, with Amanda Dossey

Amanda Dossey, SEC Ambassador with over six years of experience across sales and revenue enablement, answers the enablement community's most pressing questions about onboarding in this AMA roundup. ??

Building a successful onboarding program ??

“How do we go about building a successful onboarding program that actually works? It's overwhelming at times!?

“We have checklists that managers/employees follow and complete on their timelines, but I don't feel this is the most effective - but I also don't like to "babysit" the process. Do you have suggestions?”

Great question! When onboarding, I always feel the push/pull of what we can do in enablement versus how we can partner with sales/hiring managers.?

Before I build anything, I always start with my stakeholders. This is usually my manager and a variety of sales leaders (depending on the scope of your onboarding program).?

I do use a list, but I dig a little deeper to determine who does what and when. The accountability piece is so critical, otherwise, you definitely end up "babysitting."?

Before I meet with sales leaders, I break down the components of onboarding into what will be live and what can be done asynchronously. Asynchronous material can live in a sales enablement platform or even a shared drive.?

However, if you do have an enablement tool, it’s great because you can assign material and easily track completion!?

Live material will then be broken out into:

  • What enablement will cover
  • What sales leaders/hiring managers will cover
  • What other subject matter experts will cover?

I present this plan to all of the stakeholders and get everyone to agree on the plan.I also make sure that the sales manager's manager is involved (SVP of Sales, CRO, etc.).?

The good news is that you really only need to do this once. When everyone agrees on the framework, you can execute it as new hires begin to onboard. As things change and needs evolve, you can revisit the process above.

Once I meet with everyone and there is agreement on who does what, I book the live sessions for the new hire with each person.?

This ensures that everyone does what they agreed to do as part of the onboarding plan.?

It is a little manual, so this may not be possible depending on the size of your organization and/or the number of people on your team.?

If booking the live sessions isn't possible, you can work with the new hire to get meetings booked with their manager, etc.?

Meet with the rep once or twice weekly for a "check-in" and see what they have accomplished and where they are stuck. If they can't get the support they need, I will escalate it to management.?

I guarantee you that a rep will let you know what they need!

If you can establish a good cadence for assigning content, booking calendar meetings with SMEs and managers, and meeting with a new rep for quick touch-bases during the first few weeks/months, you will find that the need for following up lessens.?

Assuming accountability is in place, I have seen this work well. If you don't see accountability from either new hires or sales managers, that is a larger issue to discuss with sales leaders and your manager.

Which session format is best? ???

“I'd like to know: Which format do you find more effective for your onboarding experience: instructor-led, in-person sessions akin to a classroom environment, virtual sessions, online modules, or other formats?”

I am a huge fan of all formats, depending on the situation!?

Process-type content that doesn't change much usually works well as pre-recorded content that reps can view on their own time. Generally, a lot of basic "101" content can be done this way.

I like live Q&A sessions to dig deeper into topics initially covered in pre-recorded content. Let the new hire ask questions and apply what they learned in a live dialogue.?

Specific selling skills, product enablement, etc. should usually be live.?

It's always great to be in person, but it isn’t always possible, given the remote world we live in. That being said, I have found that virtual meetings can be just as effective!

Whatever you decide to do, keep it fun and interesting.?

People don't want to sit in live meetings all day (major Zoom fatigue!), but they also don't want to sit and watch videos all day with no human interaction.?

Start out with basic material in a video format that gives them the flexibility to watch it when it makes sense for them. Do follow-up meetings to discuss what they reviewed, ask them what they think, and probe for questions.?

Set up live sessions with subject matter experts for more complex topics (think discovery strategy, sales skills, call shadowing, etc).?

There should be a good balance of material to learn and exposure to actual sales calls - this allows reps to apply what they are learning to actual customer scenarios.


Looking for more great enablement content from industry veterans? Sales Enablement Collective's content hub has you covered.


“How do you determine the right blend of on-demand vs virtual training? How much role-play and pitching do you do? Shadowing? We have a four-week onboarding program and the challenge is inputting too much information to the point where advisers become overloaded.”

That is the million-dollar onboarding question!?

When thinking about onboarding, I like to break it up. There is only so much material that an adult can consume at once, so I break onboarding into phases:

  • Phase One: I focus on knowledge to support a rep through discovery and into the proposal stage. The reality is that most reps aren't going to have deals progress past the proposal stage within the first few months.?

Some may, but generally speaking, it takes several months to ramp up fully. I usually spend the first month on this phase and really get a rep comfortable with discovery, product & pricing, and demo/working with solutions consultants.

  • Phase Two: I usually pick this up in months two or three; it just depends on your sales cycle. This phase will focus on the late-stage deal process (negotiations, procurement, etc.).

However you approach this, consider what a rep needs right nowversus what can wait a few weeks/months. This gives the new rep time to digest the new material and also gives your subject matter experts some breathing room.

Choosing onboarding metrics ??

“What metrics/KPIs do you use to measure your program effectiveness? What type of content are you delivering in your program that directly impacts those KPIs? And do those KPIs change?”

Great question. When you think about metrics and KPIs, look at it in two buckets:

  • Leading indicators: content completion, knowledge check/test scores, content engagement, rep satisfaction, etc.
  • Lagging indicators: time to first call, time to first deal closed, pipeline creation, quota attainment, etc.

Leading indicators can be tracked quickly, but they miss a critical part of the picture. Lagging indicators will likely take a while to track, but they can give you a much better understanding of overall onboarding effectiveness.?

However, leading indicators are great for adjusting strategy to ensure success by measuring a rep's will to put in the work and learn. If a rep isn't putting in the work, how will they be able to close a deal?

Lagging indicators can measure onboarding effectiveness, or sometimes even a rep's ability to learn.

If you see strong leading indicators but weak lagging indicators, it is a good idea to meet with the sales manager.?

It could mean adjusting some of the onboarding program, or sometimes it can indicate that a rep is struggling to do the job. Either way, it's an opportunity to dig in and find out what is going on.


For Amanda's answers on onboarding SDRs and choosing the right stakeholders, check out the full roundup at Sales Enablement Collective.


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Aaron Spencer

Revenue Enablement Director,

1 周

Great insight as always Amanda Dossey ??

Erez H.

Senior Content and Systems Manager | Sales Enablement | Business Partner | Field Enablement | Revenue Operations | Employee Coaching | Gong.io SME | Philanthropist |Ex-Twilio, Ex-Proofpoint, Ex-Mimecast, Ex-Cofense

1 周

Welcome to 2025: The AI Revolution is Here Use AI to analyze, iterate, and automate. Businesses are still stuck paying people six figures to do five minutes of work and then spend the rest of their time convincing others why they’re needed. The ROI for AI is 10x anything we’ve done in enablement before. Onboarding? Automate it. Build a Slack Canvas or an interactive guide instead of running repetitive sessions. Give sales teams everything they need in one place—without endless emails or meetings. Measure, optimize, and automate every process so you’re not stuck spending time on what an AI agent could handle instantly. The future of business isn’t about throwing more people at problems. It’s about automating everything that doesn’t require human creativity. Welcome to 2025, where AI-driven ROI will reshape how businesses operate. You either automate—or you waste time paying for the human condition. #AI #Automation #Enablement #AIRevolution #ROI

回复
Amanda Dossey

Senior Director of Sales Enablement at Keyfactor | Ambassador for Sales Enablement Collective

1 周

Thanks for sharing! Effective onboarding is so critical for success. I always think about the “4 W’s and a H”: WHO: Who runs the training? Enablement, the manager, or another subject matter expert? WHAT: What content is critical for early success? WHEN: What content needs to be enabled on now versus what should be enabled on in 30/60/90 days? WHY: Make sure that the new hire understands why this will help them be successful. HOW: Is this onboarding virtual? In person? Asynchronous? Live? Ideally, it is a combo.

Daniel O'Dowd

Content @ The Alliance (Sales Enablement, RevOps, and GTM)

1 周

AMAs are so insightful, love seeing them hosted in the Sales Enablement Collective Slack community - fantastic answers from Amanda! ??

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