"Hiring that Great (First) VP of Sales" at SaaStr Annual 2016

BRENDON CASSIDY
VPS HACKERRANK, TALKESK,
ECHOSIGN, LINKEDIN
SAM BLOND
VPS ZENEFITS
EMMANUELLE SKALA
VPS INFLUITIVE
HOW TO HIRE A GREAT (FIRST) VP OF SALES

THE FIRST “VP SALES” PROBABLY HAS TO BE YOU
You Have to Sell It Yourself First. And Then Hire 2+ Reps.
The First “VP Sales” Probably Has to Be You
You Have to Sell It Yourself First. And Then Hire 2+ Reps.
You You + 2 Reps Hire VP Sales

Hire ASAP Once you Have  
a Repeatable Process
• Before a repeatable process =
exercise in frustration
• But just as importantly – if you
wait even one month afteryou
have Initial Traction – you are
wasting time
• Wasted time = wasted leads & lost
2nd order revenue,delay in getting
to Scale
TOO LATE IS—ALMOST—AS BAD AS TOO EARLY

Note Which One Comes Last
TOP 5 THINGS A SAAS VP OF SALES REALLY DOES
• #1 Recruiting the Team
• You’re going to need a team,  
and a good one. Quickly.
• Player-Coach sounds great — but at  
best, will be quickly obsolete as a role.
• #2 Backﬁlling and Helping  
His/Her Sales Team
• #3 Sales Tactics
• #4 Sales Strategy
• #5 Creating and Selling  
Deals Him/Herself

Source: Boston Search Group 2011
http://bit.ly/v2Sbgi
• A mediocre VPS is a cost center.  
Feels very expensive.
• But a Great VPS is Accretive
• Key: Great VPS Raises  
Revenue Per Lead
CHANGE YOUR THINKING: A GREAT VPS IS ACCRETIVE

WAYS YOUR VPS WILL INCREASE REVENUE PER LEAD
• Ask.
• Close.
• Hire.
• Sale.
• Position.
• Go Upmarket.
• Better.
• Fun.
For the Most $$$ Per Lead.
Closing is an Art – and a Science.
Better / Different Than You.
More Reps, More Quickly.
Give Prospects Right Context.
Drive to Highest Practical Deal Size
Great VPS Makes Your Product Better.
Great VPS Makes Your Product Better.

Hint: You Don’t Need New
Prospects or Customers.
• Upgrade the Team to Proven  
Closers. ASAP.
• Get the Most Out of the Inherited  
Team – And Get Rid of the Ones  
That Aren’t Working.
• Get Outbound Going.
• Close Faster & Better.
• Know How to Compete and Win.
PLAYBOOK TO MATERIALLY INCREASE SALES IN 60-90 DAYS

• You Should Know Subjectively In
Just a Few Months—Just 50% of
The Way Through Your Average
Sales Cycle
• Numbers Should Increase in 1
Sales Cycle—with Keen Focus  
on Revenue Per Lead
• First Few Hires Should be Clear
Upgrades—and made quickly  
+ seemingly eﬀortlessly
HOW TO KNOW IF YOU’VE MADE A MISTAKE

The Costs of a Bad Hire
▪ Leads Doubled in Year of Hell
▪ Yes, We Grew. But, Revenue Per
Lead Declined.
▪ Whose Fault?
• Leads Doubled in Year of Hell
• Yes, We Grew. But, Revenue  
Per Lead Declined.
• Whose Fault?
THE COSTS OF A BAD HIRE

Hire Wrong, and You’re Set Back a Year
• A Bad Hire Can Be Far Worse  
Than No Hire at All—It’s True
• A Bad Hire Isn’t Just Hard Costs—It Involves  
Huge Soft Costs As Well
• A B-level VP Sales Hires a B-/C+  
Team Under Him/Her
• Revenue Per Lead can actually  
go down dramatically
• Wastes Precious Leads, Wastes Time,  
Loss of Second-Order Revenue
• You’ll Lose a Year – At the Worst Possible Time
• A Bad Hire is Often Made Just  
as Things AreTaking Oﬀ
THE TOUGHEST HIRE OF ALL IN SAAS

YOUR VPS IS ALSO FEEDING SECOND-ORDER REVENUE
Wrong Hire = No Second Order Revenue,  
Not Just Suboptimal Sales That Year

• Hard to Get Stage Perfectly  
Right in Early Days
• Few Truly Scale Across > 1.5 Stages.
Hence, Most SaaS Cos. End Up with
Multiple VPS
DIFFERENT STAGES OF VPS. OFTEN, A DIFFERENT HIRE.

Hire ASAP Once you Have  
a Repeatable Process
• Sold at Next Year’s Target ACV –
Controls for a Lot of Variables
• Sold at Next Revenue Stage (ARR)
• Similar Competitive Selling
Background
• Outbound vs. Inbound Ratio
• First 3 People You’d Bring With You
• Less Important: Domain Expertise
KEY SCREENINGS FOR VPS

• It May Be Tempting to Hire a
Placeholder VPS – especially if
You Haven’t Done It Before
• But You’ll End Up With a Crummy
Team, and Lost Opportunities.
• Start Early. Start Now.
SO, AS HARD AS IT IS—YOU CAN’T SETTLE

• Great Sales Teams Have Low
Turnover—They Want to Stay
Together
• Great Sales Teams Feed  
on Themselves
• Great Sales Teams Energize  
the Rest of the Company
• You Just Need a Great VPS 
to Bring it All Together
WHEN IT’S GOOD—IT’S REALLY GOOD

"Hiring that Great (First) VP of Sales" at SaaStr Annual 2016

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"Hiring that Great (First) VP of Sales" at SaaStr Annual 2016