Learning From Lemkin
Top posts, insights and learnings from SaaS guru Jason Lemkin - specifically for VPs of Sales
Learning from Lemkin.
Its no secret I’m a big fan of Jason Lemkin.
In fact - after listening to multiple podcasts and consuming countless blog posts - I bought the domain stretchvp.com to embrace and share the learnings and hurdles I faced as a newly minted Sales Leader in SaaS. (check out my first - slightly embarrassing post from 2 years ago talking about the plunge).
Over the course of 2 + years, I’ve collected 2-3 floppy disks worth - or more - of content from Lemkin and found it immensely valuable for me in my role as a VP of Sales.
While most is geared specifically for SaaS founders - I consumed it all and separated the sales specific nuggets so I could come back and reference. And reference I have. Its crazy how often I’ve done this.
Naturally - I thought it may be a good idea to compile some of my favorites into its own newsletter edition. Hope you get as much value out of it as I do.
So - without further adieu - read on for more insights and learnings from Jason Lemkin including:
The Benefits of Hiring a Stretch VP of Sales
FREE SaaStr course on scaling $1M-$10M in ARR
Building Your First SDR Team (with help from Kyle Porter and Brendan Cassidy).
Plus… 14 snippets from Lemkin’s Q&A posts (Twitter, LinkedIn, Quora).
And lastly - as always, if you find this newsletter valuable- consider sharing it with someone who might as well 👊.
STRETCH SHARES
The Benefits of Hiring a Stretch VP of Sales
Jason shares a post from Brendan Cassidy (VP Sales LinkedIn, EchoSign, Talkdesk) on the benefits of hiring a Stretch VP of Sales. Ideally he looks for a VP of Sales with the following track record:
Proven Success building a team
Experience with deals in similar price range
Experience with similar sales cycle
Solid Recruiter.
But if you fall short with this stringent criteria - he recommends hiring a STRETCH!
SaaStr Scale: $1M-$10M (FREE COURSE)
Lemkin has built a reputation in SaaS as a leader that gives freely, errs on the side of the customer and can definitely walk the talk.
Check out this FREE 30 lesson course from Jason on scaling from $1M to $10M in ARR. Although pointed closely toward founders - its immediately pertinent for anyone building a SaaS Sales team. Did I mention its FREE?
Building Your First SDR Team
If you are new to building out your SDR function, I can't think of a better place to start than this AMA video and session.
Kyle Porter (Sales Loft) and Brendan Cassidy join Jason Lemkin to discuss building your first SDR Team. Gold in here - GOLD!!
STRETCH VP POST 👇
Why First Time VPs of Sales Fail (by Jason Lemkin)
Revisiting a post from Lemkin on LinkedIn (featured on the StretchVP blog last year) on the 15 things NOT to do as a first-time VP of Sales.
STRETCH SNIPPETS
Jason shows us his playbook to know if a VP of Sales candidate can really do the job.
The ultimate guide to SaaS Sales Compensation Plan
7+ Tips On How To Build Your First Sales Team with Gaetan Cachet (did he Fake it until he Made it?)
Amazing post on the 21 Top Excuses for Not Closing a Deal (follow up to THIS TWEET).
SaaS Masterclass from Jason Lemkin on scaling to $10M ARR. (Skip to 32 minute mark for VP of Sales insights)
10+ Simple Tips To Help Any Account Executive Close More.
Lemkin tells us that A Low Win Rate is Just a Huge Opportunity-in-the-Making.
What Core Metric Should VP of Sales Be Responsible For? 3 options HERE.
Lemkin’s math shows us Why a Great Rep Can Close 9x More Than a Poor Rep, and Even 2.5x More Than a Good Rep.
Loved this short article on hiring a Stretch VP early on…and why it makes sense.
One thing I’m always preaching is to assume the competitor is ALWAYS involved. Lemkin says a competitor is always trying to sell to, and steal customers and prospects.
I’m a firm believer in learned skillsets. But Lemkin talks frankly about The Difference Between Enterprise and SMB reps.
When building your comp plan - keep in mind a quota of 5x rep OTE is a great target to achieve.
Lemkin says that Great Salespeople Are Made, Not Born. But It Does Help to Start Early.
🧠 Mindset Matters
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.
Are you a VP, Director, thought leader or content producer in the SaaS space? We’d love to have you contribute. Contact Me HERE.
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