EOQ push + big co’s vs startups

In this edition: a masterclass with enablement leaders and new podcast episodes with leaders from Box and Noibu
Transparent sales process - working together
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To all those heroes making it happen – happy EOQ push! 🫡

Sending ‘Closed Won’ vibes for everyone heads down, getting those final deals across the line!

How you get to the finish line might be different, especially given the varied backgrounds of sellers + revenue leaders…

After chatting with 100’s of revenue leaders about their path to the VP or C-suite, I’ve been thinking a lot about what it takes to get there, and for better or worse, my own career choices.  

The big question - do you bet on a startup, or learn the foundations at a larger company?

From signing millions of ARR at name-brand Stripe to building the GTM team from scratch at Accord..

I can confidently say that you'll learn far more at a startup. However seeing what "good looks like" first is an invaluable stepping stone to getting it right yourself.

And it’s less risky.

At a startup you're not going to get:

  • structured mentorship,
  • documented best practices,
  • the stability most need early in their career at a pre-series B/C startup

However, if you're entrepreneurial-minded, and have top-notch grit + persistence, jumping into that early stage startup might be transformational for your career!

If not – don't undervalue the strong foundation of your craft you can build from joining late-stage or public companies that have strong training programs.

In retrospect, I'm glad I joined Columbia Records (Sony), then Stripe, then went out on my own. I don't know if I'd have made the right decisions to have made it to this point as a founder without the experience, lessons + mentorship from those previous roles.

Better to start at a big co first?

Or learn hands-on from a startup?

- Ross

In this newsletter:

  • Upcoming Masterclass -  Execution Excellence
  • 10/10 GTM Podcast - Latest episodes with Dan Wardle and Mark Wayland

Upcoming Masterclass - Execution Excellence

In our upcoming masterclass, we are diving into all things execution excellence (super passionate about this topic), and bridging the gap from enablement to the field.

I’ll be chatting with enablement leaders from Teamwork, Slack, and Databricks on April 3rd at 1pm ET. Collectively, they bring 25+ years of sales enablement experience from companies like Gong, Ada, Heap, and more.  

We’ll share proven strategies on everything from getting your team to adopt winning methodologies (hint: not just adding fields in Salesforce or MEDDIC Sheets), rolling out new playbooks, and ways to enforce your sales processes that translate to more stakeholders, velocity, and ARR.

If you’re looking to learn more about:

  • How to adopt & enforce winning methodologies with rigor
  • Rolling out new sales & CS processes that impact customer interactions
  • Strategies to guarantee org-wide adoption of your proven best practices

Then this is a masterclass you don’t want to miss!

Register here. If you can’t make it, we’ll share the recording.

April MC - Logos

10/10 GTM Podcast - Latest Episodes with Dan Wardle and Mark Wayland

A few themes have popped up when discussing operationalizing deal excellence with top revenue leaders:

  • Team leadership and mentorship
  • Multi-threading
  • Mutual Plans
  • Front-line management being one of the toughest roles in B2B sales.

With no surprise, our latest episodes with Dan Wardle, VP of Sales at Noibu, and Mark Wayland, CRO at Box also carried these themes, and I learned a ton from both of these top revenue leaders.

Episode 24 - Mutual Action Plans & Multi-threading Strategies with Dan Wardle, VP of Sales at Noibu

In this episode, Dan and I discuss his top three tips for operationalizing deal excellence across revenue organizations. We explore the importance of ironing out next steps, establishing mutual action plans, and monitoring and enforcing multi-threading.

Episode 25 - Measuring, Celebrating & Course Correcting Sales Initiatives with Mark Wayland, CRO at Box

In this episode, Mark and I discuss the importance of codifying deal excellence, partnering with frontline managers, and implementing effective strategies to measure, celebrate, and course correct sales initiatives.

Check out the full episodes on Apple Podcasts, Spotify, or wherever you listen!

There are a few upcoming episodes I am super stoked about, make sure you subscribe to get alerted when they drop!