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Jake Dunlap, CEO @ Skaled
Bowery Capital CRO Summit 2015
Optimizing Your Sales Stack
For Exponential Growth in 2016
VP of Sales at glassdoor.com
Raised over 160 million dollars
Took the company from 0-40 person sales team in 16 months
CEO of
Worked with over 40 mid-staged startups over the last 16 months
Companies have raised nearly 200 million dollars in funding and
generated millions of dollars in new revenue
A Little About Me
At Skaled, we
revolutionize
revenue
development
by transforming
clients’ sales
organizations
into machines
Demand generation to grow your
top-of-funnel with qualified
appointments
Training led by practitioners who
optimize & modernize sales
processes, technology &
organizations
Process: Advancing your
playbooks and scripting to
increase success in qualification,
proposal and closing
Technology: Assessing 21 key areas
of technology, we implement and
maximize the right systems for your
needs and goals
Organizations: Specializing roles,
making data-backed hiring
decisions, rapidly onboarding &
building a winning culture to retain
top talent.
Trends
Options
Prioritize
Implement
The Future
AGENDA
TRENDS IN 3 KEY AREAS
1.  Organization
2.  Operations
3.  Processes
Trends in the Sales Organization
Trends in the Sales Organization:
Growing Pains
29% sales orgs planning for
growth in 2016
But need to battle…..
Long ramp: 40% orgs
report 7-12 month ramp
time
High turnover: average
rep turnover now 34%
Source: Qvidian Report: Accelerating Sales Rep Ramp Time
Trends in the Sales Org:
Technology Augmenting the Sales Force
Purchases are driven by buyer
behavior & competition
Prospects are receiving more
emails and calls – takes 18
dials to connect with a buyer1
73% companies plan on sales
development tech purchase
20151
Technology will replace humans in
some areas
By 2020, 85% customer
interactions with the
enterprise will be managed
without talking to humans2
1TOPO Sales Development Technology Report
2Gartner
Source: TOPO Sales Development Technology Report	
  
Trends in Sales Operations
Trends in Sales Ops:
Data Availability vs. Data Usefulness
4 in 5 sales leaders are
challenged by the amount of
data available1
89% of salespeople are
missing opportunities due to
information overload1
4,300% projected increase in
annual data generation by
20202
Data Overload
Only getting worse…
1Lattice: Why Big Data is a Big Deal for Sales
2CSC
Predictive Analytics
Source: Gartner
Predictive hit marketing first
Moving into sales….
Source: Gartner
The Rise of Predictive Analytics
Source: Salesforce State of Sales Report
Trends in the Sales Process
Changes in the Sales Process
Changes in Models & Tech:
46% of businesses are moving to
an inside sales model1
Customer success tech à 20%
increase in up-sell revenue and
50% higher retention rates2
Growing Need for Automation:
Only 2% of cold calls result in an
appointment – and it takes an
average 6.25 hours to set 1
appointment3
Companies with automated
lead management see a 10% or
greater increase in revenue
after six to nine month4
1HBR
2Gainsight
3Buzzbuilder
4Hubspot
Source: Salesforce State of Sales Report
Know your options
Reference
Bowery Capital Guide to Startup Sales Tools 2.0
Manage & Grow Your Team
Interviewing: Take the Interview
Onboarding & Training: Grovo
Coaching & Incentives: Rivalry, Hoopla
Employee feedback: 15five, Workcompass
Focus: Technology that will streamline hiring,
make training more efficient and
comprehensive, and increase retention.
Bowery Capital Guide to Startup Sales Tools 2.0
Manage & Grow your team
Bowery Capital Guide to Startup Sales Tools 2.0
Optimize Operations
CRM & Predictive:
CRM: Salesforce
Predictive: Infer
Optimization:
Operations: Insight squared, Lattice
Data Management:
Data entry: RingLead, Zapier
Focus: Technology that allows you to automate &
analyze your pipeline, providing actionable insights that
enable quick data-backed decisions.
Bowery Capital Guide to Startup Sales Tools 2.0
Optimize Operations
Bowery Capital Guide to Startup Sales Tools 2.0
Optimize the Sales Process
Smarketing:
Social sales: Socedo
Alignment: ListenLoop, Spiderbook
Sales development:
Lead gen: Salesloft, LinkedIn, Datanyze
Email management: Outreach
Sales:
Calling: ConnectAndSell
Customer success:
Customer success: Gainsight
Customer engagement: Skilljar
Focus:
Technology that
will streamline
the sales
process, and
allow you to
better
understand and
target, with
more high-
quality
conversations.
Optimize the Sales Processes
Bowery Capital Guide to Startup Sales Tools 2.0
ASSESS & PRIORITIZE
Needs Analysis: TOF & Pipeline
Diagram Lead & Technology Flow
Talk to Your Team
Make the Decision
Selling to Leadership
Assessment Step 1:
Needs Analysis TOF
What is our ICP?
Where are our target
prospects & how do
they want to be
engaged?
How do we generate
leads? Lead flow
diagram à
VS. how do we want to
generate leads?
Source: ringio
TOF:
Assessment Step 2:
Needs Analysis
Pipeline & Metrics
What does my sales cycle look like?
What type of information do our buyers consume as they
move through their buying process?
What type of information do I need to report?
Tracking trends to determine what matters:
Stage to stage conversion rates
Average deal size
Sales Cycle
Opportunity Pipeline 	
  
Source: ringio
Assessment Step 3:
Diagram Your Technology Flow
Source: ringio
Don’t forget: talk to your team
Use tools to streamline processes and allow reps
to spend more time with prospects
Ask your team about their biggest pains
Discovery
Research
Resources: Bowery Startup Sales
Tools
G2 crowd reviews
Deciding to invest
What is
the
impact
of solving
the pain
point?
What will
the
project
cost?
How will
your
project
disrupt
existing
workflows
?
How long
before the
project
proves
ROI?
Why
should we
prioritize
over other
projects?
Most importantly:
Don’t make the investment in a new
tool unless you’re ready to also
invest in necessary training and
support to maximize the tool.
Source: Insight Squared Sales Ops Handbook
Selling to Leadership:
Proving ROI
Source: Insight Squared Sales Ops Handbook
IMPLEMENTATION & TRAINING
Sales reps waste over 50%1
of their time every day just
trying to access the tools
and content needed to
do their job
1CSO Insights
2TopoHQ
3Qvidian
Consequences of
Poor Training & Support
Only 15% of sales
technology
purchases result in
increased revenue2
Source: Qvidian Report: Accelerating Sales Rep Ramp Time
Improving Adoption
FOCUS ON THE WHY
Readily Available Materials
Use the sales training materials post training
Make sure tools and workflows are added
to sales playbooks
Build Support & Feedback Infrastructure
Make sales rep and manager interactions
work
Use metrics for reinforcement
Source: Vorsight
PREPPING FOR THE FUTURE
Prepping for the future:
Automating Calls & Analytics
Optimizing the sales
process with
automatic dialers &
predictive analytics
Takes 18 dials to
connect with a
buyer1
Source: Infer
Source: Salesforce State of Sales Report
1TOPO Sales Development Technology Report
Conclusions
Changing buyer behavior à growing need
to automate the sales process
Successful teams are already adopting
tech and you can’t compete without it
You need a process to strategically decide
on tech investments
Your systems & team must be agile to
experiment & implement new tech
You must commit to training & support
Thank you!
Email me with any questions or comments
jake@skaled.com
Follow me
@JakeTDunlap
Follow Skaled
@Skaledcom

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Optimizing Your Sales Stack for Exponential Growth in 2016

  • 1. Jake Dunlap, CEO @ Skaled Bowery Capital CRO Summit 2015 Optimizing Your Sales Stack For Exponential Growth in 2016
  • 2. VP of Sales at glassdoor.com Raised over 160 million dollars Took the company from 0-40 person sales team in 16 months CEO of Worked with over 40 mid-staged startups over the last 16 months Companies have raised nearly 200 million dollars in funding and generated millions of dollars in new revenue A Little About Me
  • 3. At Skaled, we revolutionize revenue development by transforming clients’ sales organizations into machines Demand generation to grow your top-of-funnel with qualified appointments Training led by practitioners who optimize & modernize sales processes, technology & organizations Process: Advancing your playbooks and scripting to increase success in qualification, proposal and closing Technology: Assessing 21 key areas of technology, we implement and maximize the right systems for your needs and goals Organizations: Specializing roles, making data-backed hiring decisions, rapidly onboarding & building a winning culture to retain top talent.
  • 5. TRENDS IN 3 KEY AREAS 1.  Organization 2.  Operations 3.  Processes
  • 6. Trends in the Sales Organization
  • 7. Trends in the Sales Organization: Growing Pains 29% sales orgs planning for growth in 2016 But need to battle….. Long ramp: 40% orgs report 7-12 month ramp time High turnover: average rep turnover now 34% Source: Qvidian Report: Accelerating Sales Rep Ramp Time
  • 8. Trends in the Sales Org: Technology Augmenting the Sales Force Purchases are driven by buyer behavior & competition Prospects are receiving more emails and calls – takes 18 dials to connect with a buyer1 73% companies plan on sales development tech purchase 20151 Technology will replace humans in some areas By 2020, 85% customer interactions with the enterprise will be managed without talking to humans2 1TOPO Sales Development Technology Report 2Gartner Source: TOPO Sales Development Technology Report  
  • 9. Trends in Sales Operations
  • 10. Trends in Sales Ops: Data Availability vs. Data Usefulness 4 in 5 sales leaders are challenged by the amount of data available1 89% of salespeople are missing opportunities due to information overload1 4,300% projected increase in annual data generation by 20202 Data Overload Only getting worse… 1Lattice: Why Big Data is a Big Deal for Sales 2CSC
  • 11. Predictive Analytics Source: Gartner Predictive hit marketing first Moving into sales…. Source: Gartner
  • 12. The Rise of Predictive Analytics Source: Salesforce State of Sales Report
  • 13. Trends in the Sales Process
  • 14. Changes in the Sales Process Changes in Models & Tech: 46% of businesses are moving to an inside sales model1 Customer success tech à 20% increase in up-sell revenue and 50% higher retention rates2 Growing Need for Automation: Only 2% of cold calls result in an appointment – and it takes an average 6.25 hours to set 1 appointment3 Companies with automated lead management see a 10% or greater increase in revenue after six to nine month4 1HBR 2Gainsight 3Buzzbuilder 4Hubspot Source: Salesforce State of Sales Report
  • 15. Know your options Reference Bowery Capital Guide to Startup Sales Tools 2.0
  • 16. Manage & Grow Your Team Interviewing: Take the Interview Onboarding & Training: Grovo Coaching & Incentives: Rivalry, Hoopla Employee feedback: 15five, Workcompass Focus: Technology that will streamline hiring, make training more efficient and comprehensive, and increase retention. Bowery Capital Guide to Startup Sales Tools 2.0
  • 17. Manage & Grow your team Bowery Capital Guide to Startup Sales Tools 2.0
  • 18. Optimize Operations CRM & Predictive: CRM: Salesforce Predictive: Infer Optimization: Operations: Insight squared, Lattice Data Management: Data entry: RingLead, Zapier Focus: Technology that allows you to automate & analyze your pipeline, providing actionable insights that enable quick data-backed decisions. Bowery Capital Guide to Startup Sales Tools 2.0
  • 19. Optimize Operations Bowery Capital Guide to Startup Sales Tools 2.0
  • 20. Optimize the Sales Process Smarketing: Social sales: Socedo Alignment: ListenLoop, Spiderbook Sales development: Lead gen: Salesloft, LinkedIn, Datanyze Email management: Outreach Sales: Calling: ConnectAndSell Customer success: Customer success: Gainsight Customer engagement: Skilljar Focus: Technology that will streamline the sales process, and allow you to better understand and target, with more high- quality conversations.
  • 21. Optimize the Sales Processes Bowery Capital Guide to Startup Sales Tools 2.0
  • 22. ASSESS & PRIORITIZE Needs Analysis: TOF & Pipeline Diagram Lead & Technology Flow Talk to Your Team Make the Decision Selling to Leadership
  • 23. Assessment Step 1: Needs Analysis TOF What is our ICP? Where are our target prospects & how do they want to be engaged? How do we generate leads? Lead flow diagram à VS. how do we want to generate leads? Source: ringio TOF:
  • 24. Assessment Step 2: Needs Analysis Pipeline & Metrics What does my sales cycle look like? What type of information do our buyers consume as they move through their buying process? What type of information do I need to report? Tracking trends to determine what matters: Stage to stage conversion rates Average deal size Sales Cycle Opportunity Pipeline   Source: ringio
  • 25. Assessment Step 3: Diagram Your Technology Flow Source: ringio
  • 26. Don’t forget: talk to your team Use tools to streamline processes and allow reps to spend more time with prospects Ask your team about their biggest pains
  • 27. Discovery Research Resources: Bowery Startup Sales Tools G2 crowd reviews
  • 28. Deciding to invest What is the impact of solving the pain point? What will the project cost? How will your project disrupt existing workflows ? How long before the project proves ROI? Why should we prioritize over other projects? Most importantly: Don’t make the investment in a new tool unless you’re ready to also invest in necessary training and support to maximize the tool. Source: Insight Squared Sales Ops Handbook
  • 29. Selling to Leadership: Proving ROI Source: Insight Squared Sales Ops Handbook
  • 31. Sales reps waste over 50%1 of their time every day just trying to access the tools and content needed to do their job 1CSO Insights 2TopoHQ 3Qvidian Consequences of Poor Training & Support Only 15% of sales technology purchases result in increased revenue2 Source: Qvidian Report: Accelerating Sales Rep Ramp Time
  • 32. Improving Adoption FOCUS ON THE WHY Readily Available Materials Use the sales training materials post training Make sure tools and workflows are added to sales playbooks Build Support & Feedback Infrastructure Make sales rep and manager interactions work Use metrics for reinforcement Source: Vorsight
  • 34. Prepping for the future: Automating Calls & Analytics Optimizing the sales process with automatic dialers & predictive analytics Takes 18 dials to connect with a buyer1 Source: Infer Source: Salesforce State of Sales Report 1TOPO Sales Development Technology Report
  • 35. Conclusions Changing buyer behavior à growing need to automate the sales process Successful teams are already adopting tech and you can’t compete without it You need a process to strategically decide on tech investments Your systems & team must be agile to experiment & implement new tech You must commit to training & support
  • 36. Thank you! Email me with any questions or comments jake@skaled.com Follow me @JakeTDunlap Follow Skaled @Skaledcom