30 Minutes to President's Club | No-Nonsense Sales

Creative deal structure that buyers can't resist | Mark Kosoglow

Oct 6, 2025

In this engaging discussion, Mark Kosoglow, a seasoned sales leader and former CRO who scaled Outreach from $0 to $250M ARR, shares invaluable insights on crafting irresistible deal structures. He introduces innovative tactics like meeting swaps to build trust quickly, and emphasizes the importance of flexible deal terms to win over clients. Mark also explores how to apply B2C strategies to B2B, offering creative solutions for procurement challenges. His actionable advice on turning metrics into measurable outcomes will revolutionize any sales approach!

Ask episode

AI Snips

Chapters

Transcript

Episode notes

ADVICE

Meeting Swap To Accelerate Trust

Swap value for value: offer a meeting in exchange for a meeting to make introductions mutually beneficial.
Bring concrete help (leads or sponsorships) so referrals feel worthwhile and increase trust quickly.

ADVICE

Say Yes First, Then Get Something Back

Say yes to creative buying terms first, then ask what you get in return before finalizing.
Coordinate with your manager and sell the internal case so short-term concessions buy long-term value.

ADVICE

Show The Product In Their World

Show prospects your product inside their world by mocking up dashboards or site visuals tailored to them.
Send the asset with no ask, then follow up hours or a day later to spark interest and meetings.

Get the Snipd Podcast app to discover more snips from this episode

Get the app

Huge Announcement 👉 Our next course is here: The Sales Management Operating System

Free Launch Event: Mark will walk you through his entire system, for free. You’ll walk away with more tactical leadership training in that hour than most paid courses deliver.

🎟️ Reserve Your Ticket: https://hubs.li/Q03L52Mc0

Discounted Pre-Order Access: By signing up for the event, you’ll unlock early access to our upcoming Sales Leadership Course, at the lowest price it'll will ever be.

Exclusive Toolkit: Everyone who shows up live gets access to the Sales Management Advanced Implementation Playbook, the exact internal systems Mark used to scale Outreach from $0 → $250M. This playbook has never been shared publicly. Live attendees only.

What You Need To Know:

Most new managers lead off gut — finger-in-the-air forecasting, feast-or-famine teams, and hiring that’s a coin flip.

This course fixes that.

You’ll learn the exact systems Mark Kosoglow used to scale Outreach from $0 to $250M ARR and coach 8 managers into VPs:

→ The Operating System to build a bulletproof sales process

→ The Operating Rhythm to get every rep performing like your #1

→ The Talent System to hire and ramp reps who actually hit quota

If you don’t have a system, leadership feels like firefighting.

If you do, it becomes your biggest multiplier for revenue and career growth.

To celebrate the launch of Mark's new leadership course, please enjoy a throwback to his SECOND EVER episode on 30MPC from all the way in 2023.

Four Actionable Takeaways:

B2C Mall Sales Hustle: Show them what their world looks like with your product RIGHT NOW.
When they prompt a creative deal term, say yes first, but then ask: “Does that mean you’ll buy now?” If not, keep digging.
Good creative deals lose in the short term but win in the long term. You might take the buyout hit today, but that’s ok if you keep the customer for 3 years.
When a customer asks for new product guarantees in a contract, ask: “Is what you want to be built really preventing you from achieving the result that you want?”