Shipwrecked Leadership and SDR Strategies

Shipwrecked leadership, managing SDRs remotely and the best prospecting strategies that actually work.

⚓️ Shipwrecked Leadership, SDRs and Prospecting Strategies

While this week’s newsletter has a distinct SDR theme - I’m enthralled with the story of heroism and leadership from an early 19th century explorer named Ernest Shackleton and how his experience can help us in today’s sales landscape. Cool story I’ve never heard of until now!

Come for the History lesson and stay for the leadership analogies. Plus, focused and relevant tips on leading an SDR team remotely from Sam Nelson (Outreach) and Hannah Schuler (Git Lab) and advice from John Barrows + Dough Landis on SDR outreach, prospecting and more.

We also revisit a post from Jason Lemkin on Why First Time VPs of Sales Fail (and how we can make sure we don’t get stranded in ice).

Happy Wednesday!


As always, if you find this newsletter valuable, consider sharing it 👊.

subscribe for free


🌊 What History Can Teach Us About Leading During Turbulent Times

I came across an insightful article referencing a remarkable story of Ernest Shackleton, the Antarctic explorer whose ship was locked in the ice in early 1915 and then sunk, leaving him and his 27 men to fight for survival thousands of miles from civilization. They had few material resources to rely on, save for three lifeboats, canned goods, and some stores they salvaged from the vessel. But the most important asset in surviving more than 18 months on the ice was Shackleton’s leadership, particularly the collective determination he fostered in his men to beat the odds and get home safely. How did the explorer do this? He focused on the engagement, outlook, and cohesion of the team.

Give this article a quick read - you’ll likely be back to reference these 8 key points below:

  1. Strong leaders quickly get comfortable with widespread ambiguity and chaos, recognizing that they do not have a crisis playbook.

  2. Courageous leaders also understand they will make mistakes along the way and they will have to pivot quickly as this happens, acknowledging mistakes and learning as they go.

  3. Perceptive leaders address the fear of their followers without feeding it. Ernest Shackleton called this work of the leader “dispensing mental medicine,” and it was vital to the success of his against-all-odds mission.

  4. Skilled leaders communicate frequently in a consistent format or medium. Regular communication, delivered with a certain level of energy and rational optimism, is vital in trying times.

  5. Talented leaders move deftly between presenting brutal honesty and credible hope.

  6. Strategic leaders focus on the likely outcomes.

  7. Serious leaders cultivate strong morale among their followers by keeping close tabs on collective sentiment and then responding as needed to key shifts.

  8. Great leaders emphasize the power of community. We are always stronger together than divided.

Now - when are we getting a book or movie about this amazing story?

*P.S. Check out this FREE, Harvard Leadership Lessons from Ernest Shackleton and Author Nancy Koehn. (ITS REALLY COOL)

🗣Managing SDRs Remotely - with Sam Nelson and

Highlights from Sam Nelson (Outreach) and Hannah Schuler (Gitlab) live webinar on managing SDRs remotely. HERE are the highlights in PDF form and HERE is the recorded webinar.

Sam is a great follow on LinkedIn for all things SDR and I’ve found his insight extremely valuable as I’ve put a development team together. Gitlab has made a name for themselves by being completely transparent operating a successful, 100% remote company with over $400M in funding and over 1,000 employees! Check out their core values and see why they have more than enough street cred to provide tips on what works.

Quick takeaways:

1. Culture - still do everything you are doing. Just do it virtually.

2. Be a "Handbook First" company. GitLab is notorious for this. Check out their Handbook HERE. Lots of great insight on remote policies, structure, tactics and even compensation levels.

3. Benefits of remote SDRs. See slide for specifics!

4. Landmines to look out for: Burnout, Distractions, Loneliness.

5. Tips for Communicating remotely: Assume Positive Intent and Record all meetings.

6. GitLab's Sales Stack - (see slide for details) *Remember GitLab has always been 100% remote.

7. Examples of daily cadences with Gitlab SDR Managers.

🎯What Great Prospecting Looks Like

Podcast 139: What Great Prospecting Outreach Looks Like With Doug Landis

I've seen a bunch of sales shaming online these days. COVID just made it worse. Guess what? Sales people still have quotas to hit and mouths to feed as well. Should we stop selling altogether?

Enjoyed this podcast from John Barrows and Dough Landis (*Warning: good insight, but not great language ). They talk about the good, bad and indifferent prospecting outreach they receive and how and why the best ones worked. It's easy to give sales reps a hard time for "bad" prospecting, but here's a look into what they can add into their prospecting outreach to go that extra mile and get the appointment.

You'll hear tips on: Personalization, Relevance, & Timing Writing the Right Message Empathy and Experience in Prospecting Outreach.

Perhaps polarizing opinions such as SDRs shouldn’t pitch/email C-suite (but rather have the VP of Sales send the email) and more - but definitely worth a listen.


15 second talk track that improves customer’s opinion of your sales org

Average success rate for a cold call is 1.48%. Warm them up first!

Only 48% of SDRs are consistently hitting quota. Why?


Why First Time VPs of Sales Fail (by Jason Lemkin)

At some point, we’re going to figure out how to have Jason Lemkin as a guest contributor on StretchVP. If you’re a sales leader in SaaS and don’t follow Lemkin…well…start. Here are his TwitterQuora and LinkedIn profiles to get you started. Jason has walked the talk and then some. He’s a guru in SaaS startups and Sales. He Started/Sold Echosign to Adobe for $400M and now heads his own VC fund (SaaStr Fund), SaaStr Events and one of my favorite podcasts on SaaS.

Following the recent theme of things to understand as a first time VP of Sales – I’m diving deep into the Lemkin Knowledge Well – with a post from 2 years ago. Still as pertinent today as it was 2 years ago. You can find the original post on LinkedIn Here

🧠 Mindset Matters

We see what we are focused on. In other words, we give power to what we focus on. Focus on the good. See the positive. Envision improvement. In doing so, you will see an increase in personal performance & confidence. - Riley Jensen

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.

Also… check out the blog or follow on twitter