All you can eat...
Snippets of the most popular learnings, and insights featured this year
This week…
For myself and a large portion of subscribers- this week is Thanksgiving.
Amongst many things, it also means large portions and varieties of amazing foods - as well as hot and cold takes from friends and relatives.
So…to keep things simple and on theme- this week I’ve cooked up a smorgasbord buffet with the most popular, clicked and shared snippets from some of the more trusted and noteworthy sales folks in SaaS I featured in my newsletter so far this year.
It may be a lot to digest, but read, share, and come back for seconds, or even thirds.
Happy Thanksgiving everyone! I appreciate you.
STRETCH SNIPPETS
Cold calling & emailing
⏰ “Is now a bad time?” Nick Cegelski gives us the second worst way to open a cold call. But it did leave us wondering - what’s the worst?
🎤 Ryan Scalera knocks it out of the park with this custom video to land a meeting with Gravy. Did it work? He just presented to the WHOLE team of 80!
🤔 Sam Nelson spent over a year focused exclusively on managing SDRs during their first 90 days and learned some important lessons...
🚀 “You can reach almost any CEO or executive via cold email. Yes, it works. Almost every top exec reads their email every day. If you craft literally the world-best email, it will get read by almost any leader”. - Jason Lemkin
⏳ THIS article from Qualified as well as THIS one from Hubspot provides even more validation for the “5-minute rule” for responding to inbound leads.
📞 Leave a message or nah? Mor Assouline outlines his 3 use-cases for leaving voice messages and what to say when.
⏤> Learn how to prospect with the famous Justin Michael Spear Method in this crafty infographic from Jen Ferguson and the team at InsideOut.
Negotiation
💪 Devin Reed shares his
Top 5 negotiation mistakes to maintain control over your pipeline, win more, and increase the size of your deals. Learn more about his list: Unprepared, Inadequate Information, List Price, Rushing the Process and Being too Nice.
One simple negotiation mistake (Negotiating price over email) is costing you deals. Learn what he recommends instead (sharing price over email is okay- it actually impacts win rates for the better) and more.
👉 Chris Mele, Managing Partner at Software Pricing Partners gives us his Top 9 things to keep in mind when making concessions on your next deal. My favorite: You have more power than you think.
👊 John Barrows chats with Chris Voss and shares a few takeaways from his conversation. If you haven’t read the book - listen to this podcast first for some familiar learnings like Happy Ears, Selective Listening, Win-Wins leave you vulnerable, and more.
👂 At a tactical level, sales is more like playing poker than chess says Jeb Blount. The most effective way to get a peek at those cards is to keep your ears open and your mouth shut, says Jeb Blount in this podcast about using your ears to better negotiate. “Listening is where effective sales negotiators earn their stripes.”
Selling the Problem
💪 Shawn Parrote with Chorus gives us his top 6 Objection-Handling skills: Gratitude, Empathy, Investigate, Confirmation, Value, and Proof. Plus his list of top 8 Common Objections and suggested Responses.
❌ What’s the fastest path to getting a No and why does that matter? Jeb Blount says the fastest path to a NO is to ask with assumptive confidence. The faster you get to a no, the faster you can get to a yes.
🧐 Dave Kennett says if you do this one thing well, your sales numbers will improve quickly. He says many Sales Leaders treat their teams like a Sports Team that plays games and never practices. That’s a recipe for disaster. Practice Practice Practice.
🎨 Data shows that sales reps who take control of a sale and teach their prospects how to solve their problem are more successful than salespeople who spend long amounts of time building a relationship with their lead. Check out this quick summary of The Challenger Sales Model and learn how can master the art of solving your customer’s problems.
💸 Rick Smolen talks about the customer buying process and has a good tip to prevent deals from pushing each month. “Have your buyers answer the following question: What is your response going to be when the CFO asks why are we spending $X on this?” Build on that.
Shifting to SaaS
👏 Probably one of the best guides on getting into a Software Sales career by the good folks at Lucid Chart I’ve seen.
Check out the day-to-day requirements, and career paths for SDR, AE, CSM, and other SaaS sales roles. (Note: pay scales here need to be updated)
😏 Joshua Jordan gives us 3 secrets to breaking into SaaS Sales.
📚 Ryan Robinson with Close put together this list of 31 books for leveling up your sales activity. A good stack of these are specific to SaaS - so start here and you'll be ahead of the curve.
🐝 Brandon Fluharty has successfully made the move to SaaS selling superstar. Check out his post here detailing his PREP framework with tips and secrets to help SaaS Sellers maximize success.
🧐 Kyle Coleman gives some good advice for those interviewing for their first role in tech sales.
💪 Josh Roth posts regularly about making the move into SaaS Sales. This post here is one that I point others to when I'm asked what my thoughts are.
💥 Gong gives us a solid list of ways to help turn a field sales rep into an inside sales rep (and still make quota)
Closing Deals
🧵Kyle Coleman says, on average, deals over $100k require 19 meetings with 14 different external stakeholders. MULTI-THREAD FTW.
🥇Want to win enterprise SaaS deals? It’s not always about the external sale — to the prospect. Brandon Fluharty says It’s also about the internal sale. It’s critical that you get your company rallied behind you.
😬 Jason Lemkin says the riskiest deals of all are Small Deals at Large Companies. Treat those like an unclosed opportunity and allocate resources accordingly.
🕵️♂️ Most sales are made during discovery, NOT at the closing stage of a sales cycle. So rather than pitching your product or scheduling a demo early on, pitch your discovery process first. says Ian Koniak
⏱Listen to Colin Spector discuss how to navigate landmines during a competitive deal cycle in this 30 Minutes to Presidents episode with Nick and Armand.
🧠 Mindset
"Be thankful for what you have; you'll end up having more. If you concentrate on what you don't have, you will never, ever have enough."
-Oprah Winfrey
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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