1. Gainsight on Gainsight: How the
Challenger Sale Philosophy Applies to CSM
5/4/2016

2. Child-like Joy
Ashvin Vaidyanathan
Director, Client Strategy
Philip John “PJ”
Director, Customer Success

3. Goals For Today’s Webinar
• Recap of the Challenger Sale philosophy
- How is it different from a traditional sales approach?
- How is it relevant in the subscription economy?
• Discuss ideas for how the Challenger Sale philosophy applies to
the Customer Success role
• Review best practices for applying the Challenger Sales
methodology to commercial post sales operations

4. How Does Challenger Sales Differ From Traditional
Solution Sales?
Solution Sales
• Provides solution to the
problem the customer
thinks they have
• Delivers requested
functionality
• Generally focused on
relationship
management
• Rep driven
engagements
Challenger Sales
• Teaches solution, often
to a hidden challenge
• Delivers prescriptive
solution
• Tailors message
appropriately
• Company wide effort to
create collateral, demo
orgs etc.

5. Challenger In A Subscription Economy
• In a long term subscription relationship, customer goals and
product functionality are constantly changing.
• Repeatable processAdvantages
Disadvantages
• Deprecates relationship selling
• Ignores Initial Value Moment
• Not all scenarios are analogous to complex sales

6. The Challenger Sale Philosophy Applies To Customer
Success
1. Be client outcomes focused, not client happiness focused: Bring an
outcome-driven “challenger” mindset to delivering best practices and change
management to your clients
2. Teach for differentiation: Customer Success teams have the dual
responsibility of delivering outcomes as well as creating (or enabling) content
3. Craft a multi-stakeholder adoption plan: Adoption, like the sales process,
requires delivering outcomes to multiple stakeholders across functions
4. Set the internal organizational foundations to deliver: Challenger Sale
Philosophy requires clear and frequent communications internally to ensure
escalations are managed appropriately

7. Be Client Outcomes Focused
Some observations:
• Change is never easy
• There are times when the CS team knows that the proposed
solution/direction is not the optimal solution for the client
• Clients want CS teams to be prescriptive on the suggested
solution
• Challenging a client on the right solution doesn’t always
make for a happy client in the short term, but makes for a
client that sees outcomes/value in the longer term
1

8. Be Client Outcomes Focused – Gainsight Example1
• Step 1: Strategy Session to
align on the right business
challenges to address
• Step 2: Prescriptive best
practices to address those
challenges; documented in
Success Plans
• Step 3: Track progress and
share with the client
• Step 4: Discuss learnings and
adapt processes

9. Teach For Differentiation
Some observations:
• The most impactful CS teams directly (own the creation) or
indirectly (provide input to the creation) influence best
practices and other thought leadership content
• In addition, “agile” CS teams will try new processes to
impact adoption, modify based on learnings and quickly
document it for teaching other clients
2

10. Teach For Differentiation – Gainsight Example2
Gainsight Community
aimed to drive customer
engagement & provide access to
Product team & best practices
Gainsight Webinars
Series led by Gainsight CSMs &
Administrator Office HoursGainsight Blog
Weekly posts on hot topics and
best practices

11. Craft A Multi-Stakeholder Adoption Plan
Some observations:
• Most adoption efforts are focused on the “Decision Maker”
role at the client
• Very rarely do CS teams directly focus on end-user
engagement and feedback
• Even more rare is the involvement of front line managers,
who tend to have a lot of influence on end-user adoption
• It’s also hard but imperative to involve other influential
stakeholders from other functions at the customer (e.g.,
Marketing, Support, Operations, etc.)
3

12. Craft A Multi-stakeholder
Adoption Plan – Gainsight Example
3
• Surveys to gather end-
user feedback
periodically
• Including Gainsight in
Manager workflows and
1x1s
• Involve other functional
stakeholders in
milestone meetings
(e.g., EBRs)
CS
Sales
Renewals
Support
Services
Marketing
Product
Finance

13. Set The Internal Organizational Foundations
To Deliver
Some observations:
• The Challenger approach requires a company wide effort
• It might result in not so happy customers in the short term
aka escalations
• It’s important, at least for the top tier accounts, for all the
cross-functional stakeholders to communicate on a regular
basis
4

14. Set The Internal Organizational Foundations
To Deliver – Gainsight Example
4
• Cross-functional meeting to manage escalations as one company
• Bi-weekly Key Account Team sync to discuss development –
including Sales, CS, Product, Services and Support

15. The Commercial Challenger Sale
1. Before the sales process begins, ensure alignment and applicability: It’s a
company wide effort to prepare your reps, and not every situation requires a
challenger mentality
2. There are some nuances to executing today: We still need to invest heavily in
the relationship while downplaying our own role
3. This is a team effort: Leverage Customer Success and Exec relationships to
close deals

16. Is this a Challenger Moment?
Some observations:
• Never expect a rep to develop their own content, this is a
company wide initiative.
• You need control over the message and the promised
functionality
• Some reps will default to Challenger mode.
• If the customer contact is well informed and well connected,
consider a relationship focused, solution sales approach
1

17. Gainsight Example1
• Calls to Action can identify
key cross-sell, and
transient opportunities
• Success Snapshots can
automate the Challenger
deck
• Utilization metrics can
identify sold out customers

18. Executing on the Challenger Sale
Some observations:
• The Challenger Sale was based on research conducted in
2009, when the subscription economy was still developing.
Relationships have been re-elevated.
• Your company is the expert, not you
Honestly sharing best practices can be a great dialogue
• Have you earned the right to teach?
2

19. Gainsight Example2
• Health Scores can exclude
inappropriate customers
• Manual Sentiment risks
can postpone activity
• Dashboards can balance
opportunities and monitor
conversion rates

20. Team Work is Critical
Some observations:
• You’ll be suggesting that your customers fundamentally
change how they do business. Customer Success
Managers can help to reassure the customer of success.
• Your Executive team can really help you to reach all levels
of the customer’s organization, without damaging
relationships.
3

21. Gainsight Example3
• Success Plans can
facilitate internal
collaboration
• Executive Outreach
Playbook can standardize
Executive involvement

22. Questions?