Sales Training & Coaching

Your Reps Know the Product. They Don't Know How to Sell It.

Most sales training is theory from people who haven't carried a quota in years. Elan Yudkowsky has spent the last decade in enterprise tech sales, personally closing tens of millions in annual recurring revenue — and has coached dozens of companies and C-suite executives on building repeatable, high-performance sales engines.

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$XX M+

In annual recurring revenue personally closed across enterprise SaaS and technology sales over the past decade.

Dozens

Companies and C-suite execs coached on sales strategy

10+

Years in enterprise technology sales

What We Cover

Sales Training That Actually Sticks

Not another slide deck. We work inside your pipeline, on your deals, with your reps — until the new approach becomes instinct.

Pipeline Building & Prospecting

How to build a pipeline that doesn't depend on inbound. Outbound sequences, cold calling frameworks, multi-threading into accounts, and getting meetings with decision-makers who don't respond to generic emails.

Discovery & Qualification

The difference between a demo and a deal is the discovery call. We teach reps how to uncover pain, map the buying committee, identify compelling events, and disqualify early so they spend time on deals that actually close.

Negotiation & Closing

Handling procurement, navigating legal redlines, defending price, creating urgency without desperation, and running a close plan that actually gets ink on paper. No tricks — just disciplined execution.

Sales Leadership Coaching

For founders, VPs of Sales, and CROs building or rebuilding their sales org. Hiring profiles, comp plans, forecast accuracy, deal review cadences, and building a culture where reps actually want to perform.

Sales Process Design

If your team can't describe your sales process in under 60 seconds, you don't have one. We build stage-gated processes with clear entry/exit criteria, tied to your CRM, that give leadership real forecast visibility.

Deal Coaching & Pipeline Reviews

Hands-on, deal-by-deal coaching. We sit in on calls, review proposals, challenge assumptions, and help reps develop the strategic thinking that separates quota-carriers from top performers.

Who This Is For

Built for Teams That Are Ready to Grow

Whether you're a founder doing all the selling yourself or a CRO managing 50 reps, we meet you where you are.

Startups & Founders

You've built something great. Now you need to sell it.

First sales hire coaching, founder-led sales optimization, building your first repeatable sales motion from scratch, and transitioning from founder selling to a real sales team.

Growth-Stage Companies

You have reps. They're not all hitting quota.

Team-wide training programs, individual rep coaching, pipeline reviews, and building the processes and playbooks that let your top performers' habits spread to the whole team.

Sales Leaders & Executives

You need a sounding board who's been in the arena.

1-on-1 executive coaching for VPs of Sales, CROs, and CEOs. Comp plan design, territory planning, org structure, and the leadership skills that turn a group of reps into a real sales team.

Enterprise Teams

Your deals are big. Your close rates should be too.

Complex deal strategy, multi-stakeholder selling, executive alignment workshops, and the kind of strategic deal coaching that moves seven-figure opportunities across the finish line.

How It Works

A Practical Approach to Sales Training

No binder. No motivational speeches. We get in the trenches with your team and make things better.

Diagnose

We audit your current pipeline, listen to recorded calls, review your CRM data, and interview your reps and leaders. No assumptions — just data.

Design

We build a custom training plan based on what we find. Not a generic curriculum — a program designed around your specific gaps, market, and growth goals.

Deliver

Live workshops, 1-on-1 coaching sessions, ride-alongs on real calls, and hands-on deal strategy. Everything happens on real pipeline with real revenue at stake.

Reinforce

Training without reinforcement has a 90-day half-life. We stay engaged with ongoing coaching, pipeline reviews, and measurement to make the changes permanent.

Coming Soon

Meet Elanor Labs

Elan is also the founder and CEO of Elanor Labs — a sales coaching platform that analyzes every sales interaction and helps reps improve in real time. Built from the same methodology behind EJY's coaching practice, now powered by technology.

Learn More →

Conversation Intelligence

Every call analyzed for talk ratios, discovery depth, objection handling, and next-step clarity.

Personalized Coaching

Each rep gets AI-driven coaching recommendations based on their specific patterns and performance gaps.

Manager Dashboards

Leadership gets visibility into team-wide trends, individual rep progress, and where to focus coaching time.

Common Questions

What Sales Leaders Ask Us

How is this different from other sales training?

Most sales trainers haven't sold anything in a decade. Elan is actively selling and building companies right now. Every technique we teach is something we use ourselves, on real deals, every week.

What size team do you typically work with?

Anywhere from a solo founder figuring out their first sales motion to teams of 50+ reps. The approach scales — we adjust the format (1-on-1, workshops, ride-alongs) to match the team size and maturity.

How long does a typical engagement last?

Most engagements run 3–6 months. Enough time to diagnose, train, and reinforce the new behaviors. Some clients keep us on retainer for ongoing deal coaching and quarterly pipeline reviews.

Can you train reps on our specific product/market?

Absolutely. We don't teach generic "sales skills" — we learn your product, your buyer personas, your competitive landscape, and your deal dynamics. The training is customized to how your reps actually sell.