SaaS Sales Playbook by Russ Armstrong

SaaS Sales Playbook by Russ Armstrong, updated 10/14/22, 10:06 PM

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SAAS SALES PLAYBOOK
- Russ Armstrong
An Entrepreneur’s Guide to Fundraising
RUSS ARMSTRONG
• Head of Sales - Eastern Canada, Boast.AI
• Cofounder, Limelight (>$10M raised)
• 11 years @ RBC Capital Markets
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
IN THE EARLY STAGES, COMPANIES
TYPICALLY SEE FOUNDERS WITH
DOMAIN EXPERTISE AND INDUSTRY
CONTACTS MAKE UP THE FIRST
SIGNIFICANT SALES.
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
HOW DO YOU TURN THIS INTO A
REPEATABLE SCALABLE SALES
MODEL?
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
REPEATABLE
GETTING YOUR MESSAGING
RIGHT - WHAT IS THE VALUE
PROPOSITION?
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
SCALABLE
WHAT PROCESSES DO YOU
HAVE IN PLACE THAT ALLOWS
NEW HIRES TO STAY ON SCRIPT
AND ON TARGET?
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
REVENUE 101
3 WAYS TO GROW YOUR REVENUE
MORE CUSTOMERS/USERS
(OUR FOCUS)
INCREASING AVERAGE
SELLING PRICE
INCREASING PURCHASING
FREQUENCY
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
DEFINE
YOUR
CUSTOMER
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG

Ideal Customer Profile (ICP) – Industry, Company,
B2B
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG

Ideal Customer Profile (ICP) – Industry, Company,
B2B
• Buyer Personas - job title, personality,
responsibilities, challenges, KPI’s
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG

Ideal Customer Profile (ICP) – Industry, Company,
B2B
• Buyer Personas - job title, personality,
responsibilities, challenges, KPI’s
• Value Proposition - What value does the
customer get (NOT what does your product do)
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG

Ideal Customer Profile (ICP) – Industry, Company,
B2B
• Buyer Personas - job title, personality,
responsibilities, challenges, KPI’s
• Value Proposition - What value does the
customer get (NOT what does your product do)
• What matters to this customer (Trends, FOMO,
ROI, Sales)
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG

Ideal Customer Profile (ICP) – Industry, Company,
B2B
• Buyer Personas - job title, personality,
responsibilities, challenges, KPI’s
• Value Proposition - What value does the
customer get (NOT what does your product do)
• What matters to this customer (Trends, FOMO,
ROI, Sales)
• Content (what content do you have that supports
this)
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
STYLES OF
POSITIONING
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
HEAD TO HEAD
Category exists and there is
no clear leader, easy to
understand but competition
is fierce
BIG FISH, SMALL POND
Sub-segment has unmet
needs (eg CRM for lawyers)
CREATE A NEW GAME
Category Creation, existing
categories don’t work, Most
difficult
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
VALUE
PROPOSITION
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
In simple terms, what value do
you provide to the user?
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
In simple terms, what value do
you provide to the user?
“Ridesharing marketplace”
vs
“Get a ride in 4 minutes or less”
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
Even better (S-1 Filing)
Uber says it aims to provide everyone on its
platform with a "safe, reliable, affordable, and
convenient trip within a few minutes of tapping a
button," and to provide independent drivers with
a "reliable and flexible way to earn money."
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
HOW TO -
POSITIONING
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
Competitive
Analysis
If you didn’t exist, what would
customers use?
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
Key Unique
Attributes
What features/capabilities do you
have that alternatives do not?
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
Value
What value do the attributes
enable for customers?
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
Customers
that care
Who cares a lot about that value?
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
Market to win
What context makes your value obvious
to your to your customer?
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
SALES
PROCESS
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
Stage
Attract
Convert
Close
Activate
Who
Marketing
Business Development
Representatives
Account Executives Customer
Success
Activities
● SEO
● Webinars
● Events
● PR
● Social
● Organic
● Paid

Inbound Qualification
● Outbound lead
generation
● Demo
● Workshop
● Negotiate
● Objection
handling

“Farmer”
● Grow
● Upsell
● Cross sell
KPI
● MQL
● SQL/SAL
● Opportunity
● Meetings booked
● $ Bookings $
● Upsales
● Renews
● Churn
● NPS
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
SALES METRICS
Customer Acquisition Cost
Cost of Sales + Cost of Marketing
Number of Customers Acquired
=
Average Revenue/User
Total Annual Revenue
Total Number of Customers
=
Lifetime Value
ARPU x # Purchases in Lifetime
=
CAC
ARPU
LTV
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
SALES METRICS
LTV:CAV of 3:1 or more
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
SALES METRICS
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
SALES TEAM STRUCTURE
ISLAND
ASSEMBLY
LINE
PODS
End to end – Prospect,
Convert, Close and Activate
- typical in early stage
companies
Stage Specialization,
introduce BDRs - > AEs. A
SDR team will have a
positive return if ACV is
higher than $8K
Further Specialization,
Assembly Line focused on
Channel/industry/
product/country
RULE OF THUMB: POD REVENUE MUST BE 2X POD (SALARY) COSTS.
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
SALES DESIGN
SUPERSTAR CULTURE
SYSTEM / PROCESSES
ENABLEMENT
SKILLS
SUPER
STAR
TECHNOLOGY
PROCESSES
ENABLEMENT
SKILLS
TEAM
METHODOLOGYTECHNOLOGY
SCIENCE CULTURE
GO TO MARKETA PROCESS DESIGNED AROUND SUPERSTARS VS A PROCESS DESIGNED
AROUND DATA
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
SALES PROCESS DESIGN
Local
Sales
Inside Sales
Web
Sales
Online
Sales
Field
Sales
AVERAGE CONTRACT VALUE (ACV)
DEALS / MONTH (#)$0 $1,200 $5,000 $12,500
$25,000 $500,000
$1m+
$18,000
10’s
1000’s
Transactional
Solution
Consultative
Provocative
ABM
Freemium
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
SALES PROCESS DESIGN
SELLING STYLE
HOW?
EXAMPLE
Freemium
Selling based on price/payment options
Additional features unlocked with purchase
Web Based
Selling based on your products specific solution
Very little human interaction to make a sale. Enter
Credit card and go.
Online
Selling by presenting the ways in which your product
can solve a problem
Require some online human interaction - Problem
based
Inside Sales
Most Popular - selling based on matching ICP to
problem, high touch multiple transactions
B2B, tech, SaaS, and a variety of B2C industries
selling high-ticket items.
Field/Outside Sales
B2B - Rep visit leads in person.
B2B whose sales processes rely on relationship-
building and long-term contracts.
Local Sales
Co-locating Reps with HQ. Creating multiple
champions within the organization
Enterprise sales/ multiple stakeholders. Eg ERP
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
SALES STYLE
SELLING STYLE
DEFINITION
EXAMPLE
Transactional
Product/Feature focused. Selling based on
features, price/payment options
Commoditized service with very little human interaction needed
to make the purchase
Solution
Rather than just promoting an existing product,
focus on the customer's problems and addresses
the issue with appropriate offerings (product and
services).
Selling based on your products specific solution
Consultative
Needs based Selling - Selling by presenting the
ways in which your product can solve a problem
Product knowledge is transformed into a tailored solution when
it's is delivered and positioned based on the customer's needs
and language
Provocative
Focus on identifying opportunities or problems the
customer is unaware of.
Sales people help their customers identify what they don't know
and understand the impact on the business. eg. ERP
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
ABM: ACCOUNT BASED MARKETING
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
ABM: CIRCLE
OF INFLUENCE
BUYER
FAMILY
FRIENDS
COMPETITION
PR
COMMUNITY
PAID
SOCIAL
CONFERENCE
COLLEAGUES
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
SALES FUNNEL DEFINITION
AWARENESS
EDUCATION
SELECTION
ONBOARD
USE
GROW
MQL
SQL
COMMIT
LIVE
MRR
LTV
PROSPECT
SAL
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
SALES FUNNEL DEFINITION
AWARENESS
EDUCATION
SELECTION
ONBOARD
USE
GROW
MQL
SQL
COMMIT
LIVE
MRR
LTV
PROSPECT
SAL
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
PROSPECT
Prospect is someone who we want to have a conversation with.
It is;
• Contact that converts on a top of the funnel by visiting one
of our web-assets such as our web-site
AND/OR
• a person we are reaching out to using an outbound process
The difference between the two is that with the latter following
a conversation we immediately convert into an SQL. Whereas
visiting web-assets may need further nurturing
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
MARKETING
QUALIFIED LEAD
We differentiate between MQLs based on the sense of
urgency;
• Time sensitive Calls to Action (CTA) referred to as a
hand raise such as “contact sales”
OR
• Not time sensitive such as “download whitepaper”
Both feed a different process; the Time sensitive MQL drives
the inbound LeadDev process, whereas the not time
sensitive process feeds into the outbound LeadGen process
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
SALES
QUALIFIED LEAD
An SQL always follows an actual conversation with a client in many
cases performed by an SDR. Typically this is the point that a meeting
is scheduled by the SDR for the AE.
This conversation can occur over text, email, phone call and/or a
brief meeting with the stakeholders. The SQL "Conversation call"
feeds into the sales process. At this point we know that:
• the client is a good FIT
• the client has a likely NEED/PAIN
AND
• what size is the business so we can point it to the right GTM
strategy (e.g. group and/or person to take the discovery
meeting).
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
SALES
ACCEPTED LEAD
Following a discovery call with a sales professional the AE either;
• Accepts the SQL as a qualified opportunity. This means that the AE will
be held accountable for win-rate, ACV and sales cycle,
OR
• Disqualifies the SQL either:
• by removing the SQL from the process altogether,
OR
• determine the client is not ready yet, and put them on a 90 day
nurturing program
In either scenario the SDR is held accountable for the amount of SQLs
generated and the SQL to SAL conversion rate.
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
SALES CONVERSION METRICS
AWARENESS
EDUCATION
SELECTION
ONBOARD
USE
GROW
MQL
SQL
COMMIT
LIVE
MRR
LTV
PROSPECT
SAL
Prospect ->MQL
5%
MQL -> SQL
16%
SQL -> SAL
80%
SAL -> Commit
20%
QUARTERLY
CONVERSION
RATE
RAW
QUALIFIED
MQL
10%
1000
100
SQL
16%
100
16
SAL
80%
16
12.8
Commit
20%
2.56
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
MAPPING THE BUYER JOURNEY
AWARENESS
EDUCATION
SELECTION
ONBOARD
USE
GROW
COMMIT
LIVE
MRR
LTV
PROSPECT
SAL
TOFU
MOFU
BOFU
Provoke
(Info) Graphic
Customer
Pain Story
Educational
Guide
Comparison
Guide
Calculator
ROI
Story
EMOTIONAL
EDUCATIONAL
RATIONAL
MQL
SQL
CUSTOMER INTERACTONS
Live meeting
Video message
Call
Email with image
Email with text only
E
R
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
INDUSTRY
AVERAGES
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
HOW LONG DOES IT
TAKE TO RAMP AEs?
<1 MONTH
1-3 MONTHS
3-5 MONTHS
5-7 MONTHS
7+ MONTHS
1%
19%
39%
23%
18%
Sales enablement tools have had a dramatic impact on decreasing ramp time.
Keep in mind average Rep tenure is only 2.4 years
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
PERCENT OF PIPE
SOURCED FROM OSDR
<5K
$5-25K
25-50K
$50-100K
$100K+
33%
38%
26%
19%
9%
AS A FUNCTION OF ACV
OSDR - OUTBOUND SALES DEVELOPMENT REPS
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
PERCENT OF PIPE
SOURCED FROM MARKETING
<5M
$5-20M
20-50M
$50-100M
$250-500M
32%
36%
49%
41%
COMPANIES WITH LOWER ACVS, THE CAC:LTV MATH CAN BE DIFFICULT TO
BALANCE WITH AN OUTBOUND SALES DEVELOPMENT CHANNEL.
$500M+
29%
26%
22%
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
DO I NEED AN
ASSEMBLY LINE?
<5K
$5-25K
25-50K
$50-100K
$100K+
AS A FUNCTION OF ACV
% OF AE GROUPS WITH SDR SUPPORT
73%
64 %
51%
48%
83%
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
WHAT DO I NEED TO
PAY AEs & CSMs?
2010
2012
2015
2017
100
109
118
126
BASE SALARY
$61k
OTE
$100k
MIX
60%-40%
BASE SALARY
$62k
OTE
$126k
MIX
50%-50%
CSMs
AEs
AT 100% QUOTA, AVERAGE COMMISSION RATES ARE 10% OF ACV.
AVERAGE ANNUAL QUOTA ~$770K IN ACV.
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
MEASURING PERFORMANCE
Measure the
conversion
funnel
Manage
activities not
results
Build hiring
model
ON AVERAGE, 67% OF REPS ACHIEVE QUOTA IN A GIVEN GROUP.
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
ACTIVITY
LEVELS OF
AEs
• Dials per day average 33
• Quality conversations
average 6 per day
• Demos per week averaged 7
• As you might expect, the
higher the ACV, the fewer
demos per AE per week
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
INNOVATORS
3%
EARLY
ADOPTERS
13%
EARLY
MAJORITY
34%
LATE
MAJORITY
34%
LAGGARDS
16%
EARLY MARKET
MAINSTREAM MARKET
LATE MARKET
THE CHASM
GAMIFICATION AND LEADERBOARDS
ADVANCED FORECASTING AND PIPELINE ANALYTICS
CALL RECORDING AND CONVERSATION ANALYTICS
DEALERS/CLICK-TO-DIAL
LINKEDIN SALES NAVIGATOR
CONTRACT E-SIGNATURE
CONTACT DATA AND ACCOUNT INTELLIGENCE
EMAIL AUTOMATION, TRACKING AND CADENCE
SALES ENHANCEMENT TOOLS
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
WHAT TOOLS ARE WE USING?
UNDER $250
/MONTHLY
UNDER $500
/MONTHLY
UNDER $1,000
/MONTHLY
THE MOST COMMON TRIPLE-
PLAY INCLUDES: • EMAIL
AUTOMATION, TRACKING,
AND CADENCE • CONTACT
DATA AND ACCOUNT
INTELLIGENCE • CONTRACT
E-SIGNATURE
THE MOST COMMON FOUR
TECHNOLOGIES INCLUDE: •
EMAIL AUTOMATION, TRACKING,
AND CADENCE • CONTACT
DATA AND ACCOUNT
INTELLIGENCE • CONTRACT E-
SIGNATURE • LINKEDIN SALES
NAVIGATOR
THE MOST COMMON BUNDLE
INCLUDES: • EMAIL
AUTOMATION, TRACKING, AND
CADENCE • DIALERS / CLICK-
TO-DIAL • CONTACT DATA AND
ACCOUNT INTELLIGENCE •
LINKEDIN SALES NAVIGATOR •
CALL RECORDING AND
CONVERSATION ANALYTICS
ON AVERAGE, COMPANIES REPORTED SPENDING $477 PER AE PER MONTH ON
ACCELERATION TECHNOLOGIES.
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
ARE YOU READY
FOR SALES
LEADERSHIP?
2015
2017
MANAGER
$140K
$138K
DIRECTOR
$173K
$176K
VICE PRESIDENT
$209K
$243K
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
Q&A
Russ Armstrong
416-520-8551
rarmstrong@boastcapital.com
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
WHY LEVERAGE BOAST
FOR SR&ED?
THE ONLY SR&ED AUTOMATION SOFTWARE AVAILABLE. JOIN OVER 300 OTHER
COMPANIES THAT HAVE SWITCHED TO BOAST.AI TO INCREASE CLAIMS, INCREASE
REFUNDS, FOR LESS TIME AND MONEY.
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
SAAS SALES PLAYBOOK: BY RUSS ARMSTRONG
STEP
DESCRIPTION
PREP and FOLLOW-UP
OPEN
Exchange pleasantries. Ask approval to take notes/record the call.
Ask if they reviewed the “asset” that was included in the invite.
Review LinkedIn Profiles
Include asset in Invite
ACE
Orchestrate the call, check the time, set the end goal, and engage
A Appreciate: Appreciate you taking the time
C Check time Are we still good for 30 minutes? (ask everyone)
E End goal: Typically at the end of this call, we agree to...
Ask: Does that sound right?
Determine what the outcome of the meeting is
Diagnose by probing using
Situation and Pain questions
● Ask 2 to 4 S ituational questions using context
● Ask 1 to 2 P ain/problem questions
Prepare diagnostic questions and split them up into Situational
and Pain questions
SUMMARIZE
● Summarize: So you have S and S causing you P. ?
● Ask Did I get that right?:
Prepare a list of diagnostic open- and closed- ended questions
3rd PARTY STORY
● Empathize I hear this a lot or You are not alone
● Refer to a 3rd party Mike a VP like you had the same...
Find a case study that is relevant for your client
IMPACT
Identify I mpact on the business: ↑revenue, ↓cost, improve Customer
Experience, User Experience
How does this impact you? or How does this impact your business?
Prepare a list of possible Impacts
CRITICAL EVENT
Establish a C ritical E vent: When do you need this by?

Followed by What happens if you miss that date?
Prepare a list of Critical Events that may apply
DEMO BLUEPRINT