Effective Blended Learning Techniques For Onboarding

Sales onboarding horror stories I’m sure most of us have a few.... “Familiarize yourself with our product through this one-pager and sales deck." “Meet John, our top-performing rep. Despite his busy schedule, he’ll show you the ropes.” “Here’s your login to our CRM and Gong. Play around and let us know if you have any questions.” Overlooked and overtly lazy onboarding is (unfortunately) still too common. It’s unstructured Too broad (rather than role-specific) Lacks clear learning objectives Or, even worse, it’s non-existent You can’t expect new hires to perform if you don’t lay a solid foundation for them to perform off of. This is even more heightened when you run a fully-remote sales org. What would you say is most helpful when you’re onboarding? Here’s our approach at Insightly: Balance of training types:  • Self-paced learning (ex. customer stories, webinars, Gong calls) • Live instructor-led training  • Shadowing colleagues • Collaborative group activities within the cohort Deep dives into: • Industry, market, and competitive landscape • Personas and ICP  • Identifying problems and communicating value props • Products (feature, function, use case) • Sales process  • Tech stack Learning by doing: • Elevator pitch delivery (EOW 1) • Mock CRM demo presentation (EOW 2) • Call & email cadence creation (EOW 3) • Discovery call and sales deck roleplay (EOW 4) We employ an onboarding scorecard to evaluate and gauge new hires' progress toward objectives, including a monthly bonus tied to successfully achieving training and on-the-job performance goals. Really this just scratches the surface... Every onboarding program is different. Effective onboarding cultivates confident salespeople. If you want your salespeople to be confident, you need to provide them with effective onboarding. 

Stop “welcoming” new hires. Give them a win in 30 days instead. When I first hired 8 years back, I thought the best onboarding was all about making new hires feel at home. I was wrong. New hires actually struggle with: → Understanding the business and their role. → Aligning with company culture and expectations. → Getting that first “win” to build momentum. → Building relationships with colleagues. I’ve now completely changed our onboarding process. The only goal is to get new hires to their “first win” fast. Instead of generic training, we work backward from their first big achievement. Here’s the framework: Step 1: Define the “first win” (within 30 days) Every new hire gets a specific, meaningful milestone. 1. It should be important enough that not doing it has a business impact. 2. Something that pushes them but is achievable with team collaboration. 3. It should give them real insight into how we operate. Our new Demand Gen Marketer’s first win was securing Market Development Funds (MDF) from a partner. To do this, they had to: - Work with our internal team. - Engage with a partner manager. - Propose a campaign relevant to both companies. This wasn’t just a task (it was a meaningful contribution). Step 2: Provide context (without overloading them) Most onboarding programs drown new hires in endless presentations. We limit training to what they need for their first win. 1. A 45-minute deep dive on the company’s journey, priorities, and challenges. 2. Targeted learning on only what’s relevant for their milestone. 3. Hands-on guidance instead of passive training. For the Demand Gen hire, we focused on: - Who the partner manager was and their priorities. - How the partnership worked. - What MDF campaigns typically get approved. Step 3: Align them with our work culture Culture isn't learned in a handbook. It’s experienced. Every new hire is paired with a mentor to guide them through: → Quality Standards → What "good" looks like in our company. → Processes & Tools → How we work and collaborate. → Feedback Loops → How we review, iterate, and improve. The result? New hires achieve something meaningful within their first month. They feel pride, momentum, and confidence (not just onboarding fatigue). Great onboarding isn’t about information. It’s about impact. 💡 How do you set up new hires for success?

We couldn’t ramp new salespeople in under 7 months. Then we made a few key changes—and cut that time nearly in half. Here’s what shifted: When you hire a new salesperson, they don’t come with instincts tailored to your sales motion. They bring muscle memory from other teams, other products, other customers. Sometimes that helps. Often, it gets in the way. Onboarding is your chance to teach them how to win here. That means no osmosis. No “watch and learn” from top reps. No hoping they figure it out. You show them. You write it down. You hand them the mold and teach them how to stamp. We learned this the hard way at Levelset. Early onboarding was mostly shadowing and slide decks. Reps used different demos, different intros, different objection handling. How could we expect consistent results with zero consistency in approach? So I wrote a doc: "How to Run a Demo" Then another. And another. Soon we had a full library of repeatable processes. It worked. Ramp time dropped from 7 months to 4. Quota attainment rose. Rep retention improved. Because when reps know what to do, they feel confident doing it. And confidence builds momentum. Think of it like “color by numbers” onboarding. Here’s the paint. Here’s the brush. Here’s where you start. Now go. You want a new hire closing a deal in the first 30 days. It doesn’t have to be perfect. It just needs to be a win. Wins build confidence. Confidence builds attachment. Attachment fuels effort. To make that happen, focus on four learning tracks: 1. Learn the culture. Why do you exist? What do you believe? Who are the founders? What was the first big break? 2. Learn the industry. What problems do customers face? Who are the competitors? What makes you different? 3. Learn the product. Not just features—how to demo it. How to tell stories that make it real. 4. Learn the sale. What does a qualified lead look like? What’s the process? What tools should they use—and when? Deliver this in every format: videos, docs, shadowing, recorded calls. Every rep learns differently. Make onboarding a buffet, not a single dish. And don’t wait for onboarding week to start writing. Start now. See something working? Write it down. See someone struggling? Document how you’d coach it differently. The best sales teams aren’t built on “the best people.” They’re built by turning good people into great performers—by design. That’s the mold. That’s how you build a revenue mint. ___________ I’m working on a new onboarding checklist for sales hires. If you want a copy, comment ONBOARDING and I’ll send it to you.