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7 minute read
Growing your sales team is a good problem to have. New reps mean more capacity, more pipeline and more potential for revenue growth. If your team runs on HubSpot Sales Hub, it also means an opportunity to get more people working in a system that, when used well, genuinely makes selling easier.
The question is how you get them there.
I’ve helped many B2B companies onboard their sales teams onto HubSpot, and the ones that do it well share a common trait: They treat onboarding as a deliberately designed process.
To get a broader perspective on sales team onboarding, I recently sat down with Alex Desnoyers, our Partner Development Manager at HubSpot. Because Alex works with so many agencies and their clients on these challenges every day, he has a wider frame of reference than most on what separates a smooth rollout from a rocky one.
In this post, I’ll share Alex’s practical guidance on HubSpot Sales Hub onboarding, including a helpful onboarding checklist you can use with your team. Here’s what we covered.
Think Comprehensively About Onboarding
Alex explains why so many CRM projects fail — and why it almost always traces back to onboarding.
The first thing Alex pointed out wasn’t a tactic or a tool — it was a mindset issue:
A shocking number of software implementations, specifically CRM projects, fail. Most often, it comes down to adoption. And lack of adoption stems from poor onboarding.
A big part of the problem is how companies think about onboarding. Implementation, onboarding and training are often used interchangeably, but they’re not the same.
Onboarding is the umbrella, the full process of enabling reps to use HubSpot productively. Implementation is the technical foundation — how the system is built. Training shows the sales team how to use the new tools you’ve given them.
All three matter, and all three require intention.
The system has to reflect how reps actually sell, not just what HubSpot can do. And training has to meet reps where they are, not overwhelm them with every feature at once.
When either piece is treated as a checkbox instead of a strategic decision, adoption suffers and the entire onboarding effort starts to break down.
Consult the Right People Before Building Anything
One of the most common scenarios I see: A marketing or operations team purchases HubSpot for Marketing Hub, adds a Sales Hub subscription because it’s so cost-effective, but never loops the sales team in until the implementation is complete.
Alex on what actually causes implementations to fail before the first training session ever happens.
So often the setup can look completely reasonable but doesn’t reflect how reps actually work. As Alex explained, “If the business operates in silos, the tools are going to feel siloed.”
The fix isn’t complicated, but it does require intention.
Before you finalize how the system is configured, before you design deal stages or build out workflows, bring sales stakeholders into the conversation. That means sales leaders and, ideally, two to three reps who can speak to what their day-to-day looks like.
You don’t need to give the sales team veto power over every decision; you just need their perspective reflected in how the system is built. As Alex noted, a lot of implementations fail because the tool doesn’t reflect the team’s real-world way of working.
One practical way to put that input to work: Run a small pilot before full rollout. Once you’ve initially configured the system, let a handful of reps test it. Their feedback will surface friction points in both the setup and your training plan that you’d otherwise discover at full scale, when it’s much harder to fix.
Alex clarified there’s a lot on the line to get this right: “Those little tweaks can impact whether your overall adoption rate is 50% or 90%. And the difference between 50% and 90% can be people keeping their jobs.”
That’s not hyperbole. Low CRM adoption directly affects pipeline visibility, forecasting accuracy and sales performance. The pilot step is worth the extra time.
Related Content: Is It Time to Refresh Your Team’s HubSpot Setup?
Set up the Sales Team to Succeed on Day One
Once you’re ready to bring the full sales team into the fold, some strategic prework will pay off. Alex agreed: “Your first impression is really hard to overcome.”
This made me think back to a Sales Hub onboarding project I led early in my HubSpot career. The implementation was done, and we were ready to train the sales team. I had built a beautiful but packed training agenda. If I could keep my pacing tight, I was sure we’d get through it all and the team would be off and running.
Because email is such a critical part of my client’s sales process, one of the first items on my agenda was to show the team how to send emails to leads from HubSpot. I was genuinely so excited. I just knew they were going to love HubSpot like I do!
Roughly seven minutes into my beautiful meeting, I realized I neglected to have the reps connect their inboxes with HubSpot prior to the training, and none of them had the permissions needed to complete the connection without the IT department. So this team’s first exposure to HubSpot was a bust, all due to my own lack of planning.
Alex has seen this exact scenario play out with clients, too.
Learn from my mistake! Before your first training session, make sure every rep can actually participate. Here’s a baseline checklist of items for you to complete and/or have reps do ahead of time:
- Email inbox connected to HubSpot
- Calendar integrated
- Correct user permissions assigned
- Deal stages reviewed and clearly defined
- Contact, company, deal, and ticket record layouts configured for the rep’s workflow, not just the admin’s preference
Want the full version of this HubSpot onboarding checklist?
Follow the same process we use with our own clients, so your reps are productive from day one.
Beyond logistics, this is also the moment to set expectations for what will and won’t be covered during the training. Send your training agenda ahead of the session to give your reps a framework for what they’re learning, rather than a wall of information with no context for where it fits.
Crawl, Walk, Run: Train for Depth, Not Breadth
One of the most common mistakes I’ve made myself when training reps is trying to cover too much at once. You can actually see it the moment it happens — when a helpful session turns into information overload.
While it’s tempting to want to throw everything and the kitchen sink into your training, it’s not only not helpful — it actually makes it harder for the reps to retain what you’re showing them. It’s hard advice to follow, I know. And for a sales leader who has just invested heavily in HubSpot, you may want to justify the investment by using all of the new features immediately.
Alex explains why the instinct to go all-in on features immediately is exactly backwards.
Alex’s framework for avoiding this is the crawl, walk, run approach. In the early stages of training, focus on a small number of core features the reps need the most, rather than a comprehensive tour of everything available. As Alex explained:
Being focused and narrow is more important in the short term. I’d rather have my reps getting a ton of value out of two or three things than getting shallow value out of five or six things. And over time, you may be surprised — things can grow from there.
The goal in the early weeks isn’t mastery. It’s consistency with the fundamentals: logging calls, updating deal records, working out of the contact or deal view. Once those habits are solid, you can layer in more advanced features over time.
Appoint a HubSpot Champion
Alex made a recommendation that surprised me initially but on closer reflection makes a ton of sense: Identify a peer champion.
But who?
Alex on why the right champion isn't who you might expect — and why peer-to-peer support changes everything.
Interestingly, Alex suggested it’s not necessarily your top performer. The right champion should have emotional intelligence, a natural instinct for mentorship, and the willingness to be a resource for teammates who are still learning.
Having a safe space for questions is key. As Alex explained, “It can be kind of embarrassing to ask your manager questions about HubSpot. So I might be more inclined to ask a peer who can relate to me and who can understand how that feels.”
Early in your onboarding planning process, ask the sales leadership if they have someone in mind. A good manager should be able to quickly identify the right person.
Appointing a HubSpot champion also signals to the broader team that leadership thought this initiative through and is investing in their success, not just rolling out a tool and hoping for the best.
Related Content: The Insider’s Guide to a Smooth HubSpot Onboarding for Marketing Hub
Build in Feedback Loops and Use Them
As your HubSpot onboarding process concludes, how will you know if it was successful? Alex’s answer was simple but easy to skip in practice: Ask people. “When you’re a manager, your customers are your reps.”
Alex on why how you respond when things aren't working is just as important as how you set them up.
On the qualitative side, that means conducting rep surveys and NPS-style feedback sessions at regular intervals. On the quantitative side, HubSpot’s built-in sales activity dashboards give managers visibility into whether reps are logging calls, updating deal records and doing the things the training asked them to do.
Eventually, perhaps inevitably, at some point you’ll look at a dashboard and see that a rep, or an entire team, isn’t doing what you asked. Lead with curiosity.
Before you assume it’s a motivation problem, dig deeper. Is the task hard to complete because of how the system is built? Do reps understand why they’re being asked to log a note or update a field? If the answer to these questions is no, your problem is with your process or your communication. Knowing this enables you to fix the correct issue.
“For example, if a rep has no idea why they’re being asked to do something, of course it’s going to feel like drudgery,” Alex said. Make the “why” explicit from the beginning. Connect the activity to the outcome by explaining that when we have clean deal data, we forecast better, coach better and report better. If you help the rep see that bigger picture, logging a call stops feeling like busywork and starts feeling important.
Related Content: How to Create a Scalable B2B Sales Playbook
HubSpot Onboarding Should Never Be an Afterthought
When I asked Alex to sum it all up, he landed on exactly the line that should close this post:
“If onboarding is an afterthought, and you’re just assuming things are going to go right, they rarely ever do.”
Good HubSpot onboarding isn’t complicated, but it is intentional:
- It starts well before the first training session.
- It involves the right people from the beginning.
- It focuses on a few things done well rather than everything done inconsistently.
- It stays open to feedback long after launch.
As someone who has led many Sales Hub onboarding projects — and as someone who has been brought in to fix HubSpot implementations that were poorly executed — I couldn’t agree more. You’ve spent a lot of money on your HubSpot investment, so take the time to give your onboarding initiative the care and strategic focus needed make that investment pay off.
