Bag the Elephant
Thoughts, insights, and strategies to land + expand deals in the Enterprise
Hello friends -
Maybe it’s because my team just celebrated successfully closing a large deal that had been in the pipeline for what seemed like forever (357 days to be exact) that this topic was fresh on my mind.
This deal had it all.
Numerous discovery and rediscovery. Multiple demos, technical proofing. Compliance and security reviews. Metrics. Economic Buyer vs. Champion calls. REDLINES for dayzzzzzzz.
So naturally - thought it’d be helpful to compile some topics and tactics to help us all get better at Enterprise Selling - and “Bagging the Elephant” ( good book I read several years back as I was just starting out selling and pitching larger six-figure deals as a startup- that still resonates).
In this week’s edition of Stretch Weekly -
Andy Whyte and Will Barron tell us how to win more Enterprise deals with MEDDIC
Doug Landis and others on how to sell to large Enterprises
Nick Cegelski and John Barrows discuss deal mechanics while selling to the Enterprise
Plus - loads of snippets with insights, tactics, and strategies to help you bag the elephant.
THANKS for reading!!
And lastly - as always, if you find this newsletter valuable- subscribe or share it with someone who might as well 👊.
Win More Enterprise Deals w/ MEDDIC
I’m a big fan of both Andy Whyte (Author of the book MEDDIC) and Will Barron (host of The Salesman Podcast) - especially this episode as they shine some refreshing perspective on the MEDDIC qualification framework (I wrote on MEDDIC several weeks back). Andy goes into the history, structure, what the acronym stands for (and what it doesn’t), and how to win more deals using it.
“Not all good salespeople are good forecasters, but all good forecasters are good salespeople” MEDDIC to the rescue.
No Champion, no deal. Big Champion = Big Deal.
Competition is more than just your rival solution. It’s anything vying for the same budget. I.e: status quo, internal build, rival, etc.
80% of deals won have engagement with the Economic Buyer.
NOT the same person as the Champion. Absolutely critical to be engaged with the Economic Buyer. (if not - you’re probably order taking, and not selling)
MEDDIC, as a qualification framework, helps you improve discovery. (Decision criteria, Implicating pain!)
This episode deserves to be shared, bookmarked, revisited, and repeated as there are so many good nuggets and insights. Plus…the British accents just make everything sound smarter and more believable. (just me?)
How to Sell to Large Enterprises
I stumbled upon this quick read in Forbes on selling to large Enterprises and what strategies and tactics we can use to increase our odds of success. Tom Taulii compiles a handful of compelling insights from top business leaders we should take note of.
Get Creative with your outreach
Build trusted relationships based on the company’s business and needs
Identify the pain points.
“When selling to larger companies you must come to every conversation with a point of view about their business,” said Doug Landis, who is a Growth Partner at Emergence Capital. “You have to know what they are focused on: growth, mitigating risk or cutting costs. These strategic initiatives for the business will trickle down to every department across the organization. When you know what their strategic initiatives are then it's easier to map/align your solution.”
Craft a compelling message without jargon and complex technology that targets the Champion
Land —> Expand through Freemium models
Don’t be afraid of building tailored solutions
Invest in a best-in-class sales stack to give your salespeople what they need to succeed
Deal Mechanics in Enterprise Selling
While I've been vocal about Discovery being the most important part of the sales process - and even then - a continuous, never-ending point of emphasis that Discovery can and should be used in all stages of the pipeline. But what’s next?
This episode with Nick Cegelski and John Barrows dives into detail about the in-between of those stages, moving a deal through the pipeline, and focusing on the little things to keep momentum and avoid deal slippage or silence from buyers.
If Discovery is GOAT, then arguably the next most important part of that sales process is managing deal momentum “Deal Mechanics”, specifically one of my key coachings: Next Steps. Give it a listen and learn how Nick and John get buyers to agree on next steps BEFORE the meeting even starts.
📵 Another reason to “multi-thread” your deals and get to that Economic Buyer…TrustRadius says: 50% of Enterprise B2B tech buyers will never talk to you.
🛑 How do you deal with the “not right now” objection? Jason Lemkin says to find the champion. "Budget can come from multiple places. The key is getting to the right champion, and understanding her needs."
👉 Listen to Sam Jacobs and Jacco van der Kooij role play using discovery & video to engage the Economic Buyer when you haven’t met them yet…
ᛨ Rathna Kumar details how to execute a "Land and Expand" SaaS sales strategy.
🎧 Join Devin Reed as he talks with Alex Alleyne, Strategic Sales Lead at Twilio, as he shares his approach to making marginal gains, how to balance filling, and optimizing deals in the pipeline…
🧐 To sell to the Enterprise, you need to hire for the Enterprise. Amy Volas tells us how...
🖐 Ian Koniak gives us 5 key points on how to accelerate deals so they don't get lost in purchasing...
🗣 Jake Dunlap opens up on the anatomy a deal he took from $0 to $4M in 10 months. Land —> Expand.
That’s it for this week. Thanks for reading!
My hope is if you find this valuable, consider sharing it with friends (or signing up if you haven’t already).
— Grant 👋
About stretch vp: confessions, learnings, and insights from sales leaders in SaaS
Compiled and aggregated from a network of sales leaders in SaaS, Stretch VP showcases learnings, insights, and experiences as well as best practices to overcome common hurdles, obstacles, and setbacks in your quest for excellence as a sales leader in SaaS.
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