If you're stepping into a new sales leadership role or scaling a team fast, one of the most impactful things you can do is reduce the time it takes for your Account Executives (AEs) to hit quota. It’s a topic we dove deep into on the latest Hit Your Numbers podcast with Sales Manager, Mike Day. What follows is a practical guide, shaped by real-world experience, to accelerating AE readiness without sacrificing quality.

Let’s break it down.

1. Clarity First: Set Expectations Before Day One

Most onboarding mistakes start before the rep’s first day. Sales leaders often focus too much on hiring and not enough on preparing the environment new reps are walking into.

Think of it this way: when you hire someone, they should know exactly what they're stepping into - not just their targets and title, but also the values, behaviors, and communication styles of your sales org. Mike calls this a "code of conduct," and it should be co-created with your team, not just dictated from leadership.

Before day one:

• Define what good looks like at every stage of the sales process.
• Document operating principles: how we show up, how we support each other, and how we win.
• Align mutual expectations: what the AE expects of their manager and vice versa.

This kind of clarity shortens ramp time because reps aren’t left second-guessing how things work.

2. Pre-Boarding: Start Learning Before Day One

Pre-boarding is your secret weapon. We recommend giving future AEs access to learning materials, call recordings, competitive landscape overviews, and - if possible - even access to your platform before they officially start.

Why? Because learning doesn’t have to start when the laptop opens. With 2–4 weeks between offer acceptance and start date, you can:

• Share demo recordings and onboarding decks.
• Provide access to key internal tools and documentation.
• Set light learning challenges: e.g. "Map out the ICP and bring three competitive differentiators to your first day."

That way, your new hire walks in already familiar with your world, saving you days, even weeks, of early ramp time.

3. Day One to Week Four: Get Them on the Field, Not the Bench

The old-school model of onboarding says new hires should spend 4–6 weeks "shadowing" and "learning" before touching a live customer. In reality, that’s too long. The strategy is simple: fail fast.

Get new AEs:

• Making cold calls on Day 1 (even if it’s to old leads or low-stakes prospects)
• Shadowing live deals and sitting in on demos immediately
• Practising pitch flows in front of peers and managers from week one

The trick is to make early activities safe and low-stakes. Frame every task as "practice," not "performance." But practice in public, with real consequences and feedback. The result? You build confidence and capability faster.

4. Testing and Certification: Validate Readiness

You wouldn’t let a pilot fly solo after just watching flight school videos, why do that with AEs?

Run weekly testing and certifications during onboarding. These include:

• Objection handling tests
• ICP and persona quizzes
• Role-plays for demos and discovery
• Scored trial run-throughs with live feedback

The point isn’t just to test knowledge, it’s to give reps clear benchmarks for what great looks like. When they pass, they know they’re ready. When they don’t, you’ve got a coaching roadmap.

Bonus: Give rewards for key milestones - first call, first demo, first close. Make progress fun.

5. Buddy Systems and Ride-Alongs: Learn by Osmosis

One of the biggest accelerators for onboarding? Proximity to greatness.

Ride-alongs (or live call shadowing) allow reps to:

• See how top reps prep for meetings
• Hear live objection handling in context
• Learn call structure and discovery flow organically

Even better: assign a buddy, not just for social onboarding, but for technical skills. Let the AE sit next to someone who’s done the role well and tell them to sponge up what they can.

6. Leveraging AI to Coach, Reinforce, and Scale

AI is changing the onboarding game. From document creation to 1:1 coaching, it can save hours and enhance outcomes.

Here are a few tactical ways to use it:

• Create enablement docs with AI Sales Assistants in minutes (battlecards, persona guides, email templates).
• Run role-play scenarios with AI sales bots that simulate customer objections.
• Coach on the fly with AI trained on your sales methodology, reps can get instant feedback on call plans, deal reviews, or demo prep.
• Audit your own coaching by recording 1:1s and running them through AI to get feedback on your effectiveness as a leader.

This isn’t about replacing managers, it’s about supplementing their time, especially in teams where enablement headcount is low.

7. Onboarding Isn’t Over Until Quota Is Hit (And Maintained)

A common mistake: treating onboarding as a 2-week checklist.

We recommends a mindset shift - onboarding is complete when reps are:

• Confident
• Consistent
• Hitting quota independently

That usually takes 3–6 months depending on deal cycle and rep experience.

Build structured milestones, for example:

• Week 1: First calls made
• Week 2: Basic product fluency and objection handling
• Week 4: Live demos under observation
• Week 6: Pipeline ownership begins
• Week 12+: Full quota attainment

Each stage should include a feedback loop. And importantly: keep the door open for feedback on the onboarding process itself. Your reps will tell you how to improve it for the next cohort, if you ask.

Final Takeaways for Sales Leaders

Here’s your cheat sheet:

• Clarity kills confusion: set expectations before day one
• Pre-boarding saves time: learning starts the moment they accept
• Certify readiness: don’t rely on gut feel, build testable standards
• Make it fun: games, spiffs, and mini-rewards accelerate learning
• Use AI: scale your impact and bridge coaching gaps
• Iterate constantly: treat onboarding like a product, not a project

If your AEs aren’t ramping fast enough, the problem likely isn’t them, it’s the system they’re placed into. Fix that system, and quota becomes a lot more predictable.

Want more like this? Subscribe to the Hit Your Numbers podcast or newsletter or reach out for enablement support.

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