How to Align Onboarding with Performance Goals

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.

I’ve spent 300+ hours coaching PMM through onboarding. Here is the most important tip I have: Build your 30/60/90 day plan backwards. 👇 Most PMMs' onboarding plans start with a to-do list: --> Meet with cross-functional teams --> Review past launches --> Read docs The problem with this approach is that you never feel like you’re doing enough, and everything seems equally important. You also have no real sense of how long things will take. It makes it nearly impossible to prioritize your time or align expectations with your manager. When I coach PMMs through onboarding, I tell them to build it BACKWARDS. Start at day 90 and determine, by then: – What do you want to have delivered? – What do you need to have learned? – Who needs to know and trust you? Then work backwards and chunk it down. One of my clients just joined as the first PMM at a 50-person startup. In her second week, she was already getting requests for: -> Improving the ICP and messaging -> Updating the sales enablement decks -> Building a launch strategy 😬 As you can imagine she was pretty stressed and needed a good way to set the right expectations and also plan her work. So we built a new plan, working backwards from day 90, which included: ✅ 3 streams: deliver/learn/meet ✅ Tied each project to an outcome, not just a task ✅ Chunked out each project into smaller milestones ✅ Treated learning as a deliverable, so her ramp time was visible She used that plan to align with her manager, which not only set clear expectations but also showed she could think strategically and take initiative from day one. If you’re onboarding in a startup, remember the key is not to add more, but to work backwards, and then clearly communicate that to set the right expectations. Let me know how I can help. 💪 #productmarketing #newjob #coaching #strategy

Enablement is NOT Checklists Let’s be honest: Too many enablement teams get stuck checking boxes (training delivered, content uploaded, certifications completed). But enablement’s real value isn’t in check the box exercises. Rather, it’s accelerating your company’s North Star. If your org’s 2025 goal is to “increase enterprise deal size by 30%” or “reduce churn by 15%” enablement must be the engine that turns that vision into seller behaviors and customer outcomes. Here’s how: Step 1: Align to the North Star What’s the ONE business outcome your leadership cares about most right now? - Revenue expansion? - Market share in a new vertical? - Customer lifetime value? Enablement’s role: Translate that goal into specific seller competencies. Example: If the North Star is “50% revenue from cross-sell,” enablement must equip reps to: - Identify cross-sell triggers in discovery. - Overcome “buyer indecision” objections (think The JOLT Effect Matt Dixon Ted McKenna) - Co-build ROI cases with champions. Step 2: Define Enablement KPIs That MATTER Forget “hours of training delivered.” Tie enablement success to business KPIs your CRO & other leaders care about: - % of reps exceeding quota (enablement’s job: skill gaps closed). - Deal velocity in priority segments (enablement’s job: applying credible & actionable playbooks for stickiness). - Customer retention rate (enablement’s job: equipping CSMs to spot risk signals) Step 3: Correlate impact beyond “Butts in Seats” Enablement leaders often struggle to prove ROI. Shift the conversation with data that links learning to outcomes: - Pipeline Impact: How did negotiation training affect average deal size? - Behavior Change: How often are reps using the new discovery framework and where is it driving velocity? - Customer Outcomes: How did the onboarding adjustments reduce time-to-value? The Bottom Line: Enablement Is a Strategic Lever, Not a Cost Center When you anchor to the North Star, enablement becomes the bridge between leadership’s vision and frontline execution. Your Move: This week: Ask your CRO/CEO:  - If you could only track one metric, what would it be? Or, What’s the number that, if it trends wrong, will haunt your next earnings call? - Why it works: Links metrics to real-world consequences (investor pressure). This quarter: Build an enablement KPI dashboard that mirrors it. Partner with your Rev Ops or Business Ops team to help you! #oneteam #SalesEnablement #RevenueOperations #Leadership

How do I build a 12-month roadmap for a recruit using their production and my company playbook? Let me share a quick story. One of the leaders I coached was struggling to onboard a new hire effectively. They had great potential but didn’t quite understand how they fit into the big picture. As they dove into the role, the rookie felt lost and overwhelmed, leading to a few early missteps. We worked together on a solution. Instead of just assigning tasks based on numbers and quotas, we flipped the script. We created a detailed 12-month roadmap aligning their production goals with our company playbook. This wasn’t just about selling; it was about grasping our vision and understanding how their contributions would make an impact. Here’s how you can do the same: Start by identifying key production milestones for the recruit, breaking them down into manageable quarterly goals. For each quarter, align these objectives with specific elements of your playbook — training modules, key projects, or team collaboration opportunities. Ensure that each milestone has clear, actionable steps and reasons behind them, so the recruit knows not just what to do but why it matters. Also, keep communication open. Regular check-ins will help you both stay aligned and pivot if necessary. This framework works because it transforms the onboarding experience from a transactional series of tasks into a collaborative journey. When recruits see how their efforts support a greater vision, they’re not just going through the motions; they’re genuinely invested in the success of the team and the company. A meaningful onboarding process can set the stage for long-term engagement and high performance. Let’s make sure our new hires feel they belong and can see the roadmap to their success right from the start.