Key Takeaways
- Effective sales onboarding is a structured transition from learning to doing—not a two-week classroom event
- Break the first thirty days into four phases: Foundation, Skills, Application, and Independence
- Include checkpoints at the end of each week to validate competency before progressing
- Use AI for on-demand knowledge access and roleplay practice to accelerate skill development
A new sales rep just started. The clock is ticking. Every day they're not productive is a day of salary without revenue.
But push them into calls before they're ready, and they'll fumble opportunities, damage prospect relationships, and lose confidence that takes months to rebuild.
The traditional approach—weeks of training before any customer contact—doesn't work. Neither does throwing them in the deep end on day two. For a deeper look at rethinking the fundamentals, see our sales training playbook.
The answer is a structured ramp that gets them into real work quickly while building knowledge and skills systematically.
Here's a 30-day plan that balances speed with readiness.
Week 1: Foundation
The goal: Understand enough to have basic conversations. Start observing real sales interactions.
Day 1: Orientation and context
Start with why, not what. Why does your company exist? What problem do you solve? Who do you solve it for? What makes your approach different?
A rep who understands the mission can improvise when conversations go off-script. A rep who only knows features will be lost the moment a prospect asks, "Why should I care?"
Also cover the basics: systems access, team introductions, how things work around here. Remove friction so they can focus on learning.
Days 2-3: Product fundamentals
Not everything about the product—the core. What does it do? Who uses it? What are the primary use cases? What are the most important features, and why do they matter?
Keep it focused. They'll learn the long tail of features as they encounter them. Right now, they need enough to understand what they're selling.
Pair this with hands-on time in the product. Reading about features isn't the same as using them. Have them complete common workflows, set up a demo environment, experience the product as a customer would.
Days 4-5: Customer and market
Who buys this? What are their titles, their challenges, their goals? What does their buying process look like?
Cover your ideal customer profile, common personas, typical buying journey. Include a competitor overview—not deep battlecard detail yet, just awareness of who else is in the market and how you're different.
Have them listen to recorded sales calls. Not to evaluate—to absorb. What do conversations actually sound like? What questions do prospects ask? How do experienced reps handle them?
End of Week 1 checkpoint: Can they explain what your product does in two minutes? Can they describe who typically buys and why? Have they listened to at least five sales calls?
Week 2: Skills and process
The goal: Learn your sales methodology and start practicing core skills.
Days 6-7: Sales process and methodology
Walk through your sales process stage by stage. What happens in each stage? What's the rep's job? What qualifies a deal to move forward?
If you use a specific methodology—MEDDIC, Challenger, SPIN, whatever—introduce it now. Not as theory, but as practical guidance for how to run deals.
Cover your tools: CRM workflows, what to log, how to track deals. Make expectations clear so good habits form early.
Days 8-9: Discovery and qualification
Discovery is where deals are won or lost. Spend real time here.
What questions should they ask? How do they uncover pain, understand priorities, identify decision-makers? What does good discovery sound like?
Practice. A lot. Have them practice discovery calls with teammates, with you, with AI roleplay. Get repetitions. A rep who's practiced discovery twenty times will sound different than one who's done it twice.
Day 10: Objection handling fundamentals
Introduce the most common objections they'll face. Price, timing, competitor, status quo. What's the framework for handling each one?
More practice. Objection handling is a performance skill. They need to hear themselves respond, get feedback, try again.
End of Week 2 checkpoint: Can they walk through your sales process correctly? Can they conduct a basic discovery conversation? Can they handle the top five objections with reasonable responses?
Week 3: Application
The goal: Start real customer interactions with support. Apply learning to actual situations.
Days 11-12: Demo and presentation skills
How do you present the product? What's the structure of a good demo? How do you tailor it based on what you learned in discovery?
Practice presenting. Record it. Watch it back. Identify what works and what needs improvement. Repeat.
Days 13-14: First live interactions (supported)
Time to get on real calls—but not alone. Options depending on your model:
- Shadow a senior rep on live calls, with defined moments to participate
- Handle inbound inquiries with a senior rep listening and available to help
- Co-lead calls with their manager, taking specific sections
The goal is real customer interaction with a safety net. They're in the game, but support is right there.
Debrief every call. What went well? What would they do differently? What questions do they have? The debrief is where learning happens.
Day 15: Midpoint assessment
Formal check-in. How are they doing? Where are they strong? Where do they need more work?
This isn't pass/fail—it's diagnostic. Use it to focus the remaining two weeks on what they need most.
End of Week 3 checkpoint: Can they deliver a basic product demo? Have they participated in at least three live customer interactions? What specific areas need focus in the final week?
Week 4: Independence
The goal: Run deals with decreasing supervision. Build toward full productivity.
Days 16-18: Increasing autonomy
More live calls, with progressively less hand-holding. They lead, manager observes. Then they lead, manager is available but not in the room. Then they're on their own with debrief afterward.
Ramp up responsibility as they demonstrate readiness. Some reps move faster than others—adjust based on what you're seeing.
Days 19-20: Pipeline building
If your role includes prospecting, this is where they start in earnest. Teach your prospecting approach—email, phone, LinkedIn, whatever your playbook includes.
They should be building their own pipeline, not just working handed leads. This is where self-sufficiency begins.
Days 21-22: Deal management
They should have active opportunities by now. Teach them to manage a pipeline—prioritization, next steps, when to push, when to be patient.
Review their deals. Ask questions that develop their deal sense. What's the path to close? What could derail this? What do you need to learn? What's your next step and why?
Pipeline hygiene as habit: Emphasize that CRM hygiene is not administrative busywork—it's a forecasting tool. If a next step isn't logged with a date, the deal is considered stalled. By instilling this discipline in Week 4, you prevent the common "ghost pipeline" problem where managers can't see reality.
Days 23-25: Refinement and practice
Use the remaining days for targeted development. Whatever gaps emerged in week three, address them now.
More practice on weak areas. More call observation and feedback. More repetitions on objection handling, discovery, or demos—whatever needs work.
End of Week 4 checkpoint: Can they run a complete sales cycle (with complex deals still escalated)? Do they have an active pipeline they're managing? What development areas need ongoing attention?
Day 30: Launch
They're not fully ramped—that takes longer than thirty days. But they should be:
- Running their own calls with confidence
- Building and managing their own pipeline
- Handling common situations independently
- Knowing when to ask for help on complex situations
The remaining ramp happens through experience, coaching, and ongoing development. But the foundation is set.
What makes this work
- Learning and doing interleave. They're not learning for two weeks then doing. They're learning and doing from week one, with the mix shifting toward more doing over time.
- Practice is built in. Real skill development requires repetition. This plan includes deliberate practice throughout, not just information transfer.
- Checkpoints catch problems early. Regular assessments surface issues while there's time to address them. A struggling rep identified at day fifteen can get help. One identified at day forty-five has already burned opportunities. When evaluating AI simulation versus live training, use both strategically at different stages.
- Flexibility within structure. The framework is consistent, but you adjust based on the individual. A rep with industry experience might move faster. A rep struggling with discovery gets more practice time there.
Supporting the plan
A few things make execution easier:
- Make knowledge accessible. When they have questions—and they'll have many—they need answers fast. A knowledge base, an AI assistant, or clear documentation beats waiting to ask someone.
- Assign a buddy. A peer they can ask the questions they're embarrassed to ask their manager. Someone who remembers what it was like to be new.
- Manager involvement matters. This isn't something to delegate entirely. The manager's participation in week one, in call debriefs, in checkpoints—it signals that development is a priority.
- Track leading indicators. Don't wait until quota attainment to know if onboarding worked. Track calls made, pipeline built, conversion rates early. Intervene fast if something's off.
Thirty days doesn't create a fully ramped rep. But it creates a rep who can function, contribute, and continue developing through experience.
The investment is structured time upfront. The return is faster productivity, fewer lost opportunities, and reps who hit their stride sooner.
Your next new hire starts soon. Be ready.
JoySuite accelerates sales onboarding. Product knowledge available instantly, whenever reps need it. AI roleplay for unlimited practice on calls, objections, and scenarios. Assessment that verifies readiness, not just completion.
