The Sales Playbook for 2022: A Deep Dive with Brendon Cassidy + Jason Lemkin - The Entrepreneurial Way with A.I.


Saturday, November 6, 2021

The Sales Playbook for 2022: A Deep Dive with Brendon Cassidy + Jason Lemkin


The other day Brendon Cassidy, the first head of sales at LinkedIn and the first VP of Sales at $10B Talkdesk, Adobe Sign / EchoSign, and more — and now co-CEO of Cosell — and I caught on what’s changing in the Sales Playbook for 2022.

It’s a great deep dive you can watch here.  My Top 10 Learnings below:

  1. The classic high volume cadence-based outbound playbook is declining in effectiveness — but you still need to run it.  This was a great insight.  We’ve all seen the performance of mass cadences and barely-personalized emails decline.  Brendon’s point is you need to add to that strategy — it’s not enough anymore.  But that doesn’t mean abandon it.  It still works.  Just not nearly as well as a few years back.
  2. Your VP of Sales needs to own outbound themselves, including directly hiring and managing the first SDRs.  Brendon says the toughest hire is a “Director of Outbound” these days and that’s what I’ve seen as well.  You can’t outsource great outbound, and a VP of Sales that’s not good at it or has never done it can’t just go find a unicorn Director of Outbound.  These days your VP of Sales has to roll up their sleeves and get that outbound engine going themselves — including the first SDRs.  And some of them won’t really want to do it.
  3. Top CROs and late-stage SVPs of Sales are getting better and better at retaining that first VP of Sales that got the company to scale.  Brendon seen at Gong, Outreach and other leaders that the first VP of Sales stays basically in that role for as long as possible.  The best CROs and such don’t replace a winning leader — they augment them and help them scale further.
  4. ABM isn’t a failure — it’s just you can’t turn it all into software.  There’s lot of talk these days about ABM not working, but it’s not ABM that’s failed, rather it’s not doing the work.  Hyper personalized outreach that deeply understands the specific needs of a prospect still works.  Well in most cases.
  5. Everyone needs an outbound team now.  Sales is being pushed more and more not just to close leads from marketing, but source more and more of its own customers.  Even in SMB and mid-market.
  6. An interim VP of Sales can work — if it’s done right.  Brendon’s done it himself and seen it work.  Key it often narrowing their spec — i.e., just do inbound.  And getting a time-based commitment, e.g. a year.  4 days a week from a top candidate with a narrow spec can be a lot better than no VP of Sales at all.

Much more in the great convo above!!

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Jason Lemkin, Khareem Sudlow