But no topic has inspired and challenged me like this one…
To share some of what I’ve learned from the experts, I’ve pulled together my Top 11 from the past 12 months for you. I hope that they inspire and challenge you, too.
1. The Art of Making Love by Jacco van der Kooij (Winning by Design)
Change your language to change your mindset. You’re not “spearfishing” (which would imply you’re killing your customers… Nice one, guys). Instead, you’re Educating, Committing, and Assisting them.
It’s about “You” not “Me.” By putting your customer truly in the center, you’re making your job easier — and more fulfilling. Win win.
Learn more about Winning By Design
2. Sales Under Pressure with Erika Shumate (Pinrose) and Harrison Metal
Preparation trumps personality. When she decided to sell her product Pinrose on QVC, Erika Shumate learned that sales was about relentless practice and preparation more than her personality.
When you’re selling perfume to strangers through a (scent-free) screen, you’ve got three key levers:
- Language: turn a “perfume sample pack” into “fragrance wardrobe”,
- Demo: touch the product, use it, show your love for it, so the customer can follow and
- Power of “Yes”: taking a page out of the improv playbook, always be building. Replace that “no” with a “yes, and!” so you never shut it down.
3. The XYZs of Selling with Jeffrey Gitomer
The New Sales is about Relationships. Jeffrey Gitomer offered dozens of tactical tips in this rapid-fire session, but what left the deepest impact was his infectious obsession with constant learning. “Base everything off of the person you want to become.”
Build relationships by finding the pleasure, not the pain. Make your questions emotional: replace “Where are you from?” with “Where do you grow up?” Relationships first, and sales will follow.
4. How to close $X00,000 [BIG] Deals with Amy Pressman (Medallia), Andy Byrne (Clari) and Aaref Hilaly (Sequoia Capital)
#1 thing? Be fearless. Just because selling big deals as a small startup might be scary for you, doesn’t mean that it scares your customers. So be confident.
As Amy Pressman put it, the core here is intellectual honesty. Is your product really worth it? Until you believe that, selling those zeros will be hard. But when you have that conviction, you can do anything.
5. How to Prospect with John Barrows
The death of the (average) salesman. The average salesman is dead because AI is killing — has already killed — him. With insanely rapid advances in technology, AI is replacing more and more SDRs’ jobs.
So if you’re a SDR what do you do to fight for your job against the Tech? Be more human. What can AI still not do? Tell a story. Pick up the phone and tell them a story. Be human, and keep getting better if you want to survive.
6. Using AI to Beat Competition with Jensen Harris (Textio), Puneet Mehta (msg.ai), Derik Pridmore (Osaro), and Matthew Zeiler (Clarifai)
AI’s potential is in augmentation, not automation.
A year ago I wouldn’t have tagged this as a “sales” talk, but on the heels of JBarrows… you can’t think about sales without looking at technological advances in the tools we use everyday to sell.
And things are changing. Quickly. Jensen Harris, CTO of Textio, described just how broad this reaches.
“If you don’t have learning loops in your software in five years, it’s defunct. It’s dead. It’s like not having internet connectivity.”
So as salespeople, we have to prepare for — and embrace — this new normal. While AI won’t automate our jobs, it’s going to augment our work every day.
7. B2C vs. B2B Growth by Lauren Vaccarello (Box) and John Hurley (Radius)
Content is critical… especially when you have multiple buyers.
The more complex the sale, the more Marketing and Sales are blending. With a shifting funnel, content becomes the job of your sales reps, too. And that’s why you need a robust playbook that’s buyer centric.
8. The Art of Disqualification with Mary Ann Wofford (Heroku), Katherine Andruha (Apttus), and Brian Schwartz (UserTesting)
Setting up a culture where it’s ok to fail matters if you don’t want to waste time on bad customers or bad leads. Good reps are always qualifying, not just closing.
Unqualified Customers = Unhappy Customers = Detractors.
Qualified customers = Happy Customers = Referrals.
9. How Pirates, Dreamers and Innovators Create and Dominate Markets with Al Ramadan
Don’t sell a product, create a category.
Use the grocery story metaphor to frame your approach. Are you selling a product in the aisle? Or are you creating a new aisle altogether?
Winners do the latter.
10. Secrets of the 100M Club, Dan Levin (Box), Dave Girouard (Google Enterprise) and Marc Diouane (Zuora)
“You can’t feed an army hunting squirrels.”
If you want to make it big, you’re going to have to go big. While “hunting squirrels” might get you to $10M in ARR, it won’t get you to $100M. Going big is hard, but you’ve got to do it.
11. The New Power Couple, with Kristen Malkovich (Mktg @ Chorus) + Rob Perez (Sales @ Chorus) and Dayna Rothman (Mktg @ Brightfunnel) + Zack Kass (Sales @ Brightfunnel)
If those are different across departments, don’t expect the departments to work well together. Think about that scorecard: MQLs or SQLs? Metrics matters. The more you can close the gap, the better.
Who has taught you the most about Sales this year? Give them a shout out.
Originally published at Sales Hacker.