Streamlining Onboarding Processes for New Sales Reps

You finally land a rep. $150K OTE. $15K in recruiter fees. $5K on tools, tech, swag. And they don’t fully ramp for 6 months. Then churn in month 14 lol. That means you spent 10 - 12 months paying CAC for a rep that gave you 2 quarters of yield. Congrats - you just lit 30% of your customer acquisition budget on fire! 🕺 Let’s break down the math a tiny bit: - Avg ramp time = 5-6 months. - Avg tenure (esp. post-COVID) = 14-18 months. - Which means ~40% of their employment is ramp. - And if they never become top performers, you never recover the CAC. This is more of a design issue than a rep issue. Why? Because most onboarding programs are still built like it’s 2015. Here are a few ideas of what to do differently: 1. Teach outcomes, not org charts. Week 1 shouldn’t be 42 slide decks and a parade of “meet the team.” You want reps to ship value fast. That means: - Role-based onboarding tracks. - Call listening and deal review by Day 3. - One real buyer-facing output by end of Week 2. Most onboarding doesn’t fail from lack of content. It fails from lack of intent. 2. Measure progression like pipeline. You don’t manage deals by feels. Stop managing rep ramp that way. Track: - Time to first meeting booked. - Time to first qualified op. - Time to first closed deal. - % of milestone behaviors completed by Week 4 / Week 8. If you can’t see it, you can’t coach it. And if you’re not coaching it, you’re just hoping. 3. Don’t wait until Month 6 to inspect performance. Ramp is not a free pass. It’s a pattern detector. By Week 3, you should know: - Are they consistent in activity? - Are they asking layered discovery questions? - Do they understand the buyer, or just the product? Onboarding is not “set it and forget it.” It’s “inspect and iterate weekly.” 4. Align managers lest nothing sticks. If enablement teaches one thing and managers coach another, reps will default to survival. You want: - Managers running onboarding check-ins every week. - Deal reviews tied directly to onboarding concepts. - A shared view of “what good looks like” across the first 90 days. Onboarding doesn’t end with a checklist. It ends when reps think like your buyer and execute like your top 30%. tl;dr = most onboarding isn’t too light. It’s too slow, too generic, and too detached from actual revenue motions. Fix that, or keep watching CAC go up while rep yield stays flat.

Within 10 months, I lost all 8 of the new AEs we'd hired. I'd failed them in ramping, and that's when I went on a 4 month deep dive to fix AE ramp that resulted in a 23 page paper with key changes to make. Here are a few: 1. 2 daily standups for 3 months Morning and end-of-day meetings to answer 2 questions: - 3 things you need to get done today? - Did you get your 3 things done yesterday? Why? I got to understand how people were thinking about what's important and how well they were focused on executing it. I could guide an AE into the right work daily. 2. Faster starts We had 4 or 5 gates rampers had to clear to get SDR meetings. It would take a 2-3 weeks+ to start getting meetings. This was too slow, so we gave AEs small, inbound meetings on week 2 of onboarding. Why? Wins beget winning. AEs won these deals and felt themselves a bit! It was OK if they blew a couple small ones to get the coaching and feel for what was needed to win. 3. Groups vs one-offs We moved to classes of 3+ hires at a time. Reps that start alone feel lonely, like nobody is quite where they are. Why? Having a "ramping classmate" is a huge help bc they are suffering what you are suffering, worrying about what you are worrying about. Having a peer to share with helps and creates relationship. 4. Specific certifications We created disco and demo certifications that were hard to pass. They could get the small inbounds before being cert'd but not their book of business being worked by SDRs. Why? Having a tangible level of confidence around 2 foundational parts of the cycle helped make sure we didn't waste buyers' time and that AEs started with a known, successful flow. 5. Ramp comp We created the ability to hit accelerators on a ramp quota. Several reps make stacks of cash exceeding their ramp which meant they worked hard to get their certs and accounts going. Why? What's more important than early momentum in a sales job -- not much. Getting wins, making a fat check to start. Those lock you in to working harder. 6. Vacant territory policy We created territories ahead of hiring and "loaned" them to existing AEs to work. We'd let reps hold onto accounts they got into to close them to be fair. But, that led to reps walking into territories with multiple opps being worked which limited the accounts AEs could start with. We ended up creating a policy where vacant territories could be worked by existing reps (we assigned them out), but any deal that was open when a new hire started was immediately split 50/50 and the experienced rep would mentor the new hire through the deal. We then had some SPIFFs, too, for the existing reps to help here. Why? Great way to see what good looks like and existing reps worked deals harder to get them closed before rampers go hired. ♻️ Consider reposting if you've a bad ramp cost you a good job. ❓ Have you ever had an amazing ramp period?

Our new sales reps regularly close deals their first week on the job. The secret is a simple document we create before they start. This One-Pager contains: → Clear expectations and KPIs → Every resource they need → Daily action plan → Scripts and objection handlers → CRM process documentation → Call recordings to study → Company wins and case studies All accessible in ONE place. We create a One-Pager for every role (SDRs, closers, customer success, everyone). Your salespeople can't execute what they don't understand. And they can't find resources scattered across Google Drive, Slack, and your CRM. Give new hires crystal clarity on day one. Not just about what to do, but how to do it and where to find everything they need. If your sales onboarding takes more than 3 days, consider reevaluating your process.

I scrapped our entire SDR onboarding program at 9AM on a Monday. By Wednesday, a new hire booked his first two meetings. Last year, I hired a new SDR leader, Alex Choi. One of the first things he told me was: “First-week onboarding is bullsh*t.” And he was right. Here’s what most SDR leaders don’t get: Your onboarding is not about information. It’s about speed to action. So Alex’s first day we killed our 10-day SDR onboarding program. Now our SDR onboarding looks like this: Day 1: Listen to real sales calls, 2-hour onboarding session, role play, 2 hours of product training. Day 2: Start Dialing No more wasting 10 days on tools, internal decks, product docs. The goal is immediate, structured action with rapid feedback. Not slide memorization. Our new SDR Gautam Srinivasan joined last month and booked 2 meetings on day 2. The faster you can get reps into real work, the faster they learn. And the more meetings you book. Not everyone will agree with this, and it certainly depends on the industry. I wouldn't put SDRs on the phone for a highly technical cybersecurity software. But for a TON of companies out there this approach would help you onboard reps faster and let them learn in the market.

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?

If your new sales reps are still struggling 90 days in, it’s a leadership problem and not a talent issue. Most onboarding is a performance delay, not a ramp-up plan. During my first week in sales, I was told to just watch these videos and read the playbook. That is how many organizations fail their salespeople in the first 30 days, not because of bad intentions, but because of bad onboarding. Sometimes, leaders who assume their reps just need more time. But time isn’t the problem. The onboarding process is. That's what I call the “sink or swim” approach: Throw new hires into product decks, shadowing calls, and systems training You can’t expect sales reps to win deals if you don’t give them the tools to succeed. When I work with sales leaders, we focus on onboarding that actually drives outcomes and prepares them to sell. Here’s what that looks like: --> Skill-building assignments like competitive analysis and SWOT, not just content consumption --> Shadowing cross-functional teams to understand how value is delivered, not just pitched --> Structured reflection so reps can process what they’re learning and apply it immediately --> Live assessments where managers check for understanding, not just completion. And the result? More confident reps, shorter ramp time, and better collaboration across the company. The sooner your reps build the right habits, the sooner they produce. PS. What are you doing to solve this problem?