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How a Developer Builds a
Sales Team
(Scaling Sales the Agile Way)
Jeff Szczepanski, COO
What is the Objective?
Objective
Predictable
Revenue that is
Scaling Fast
(Building a Billion Dollar Company)
What is the Plan?
Typical Startup Plan
1.Idea!
2.Technical Co-Founders
3.Raise Money
4.Build Great Product
5.Hire Head of Sales
ie: ‘Needz Sales’
6.Profit!!
Typical Startup Outcome
1. Idea!
2. Technical Co-Founders
3. Raise Money
4. Build Product
5. While( Cash Remains )
Hire Head of Sales
<some stuff happens>
Wait 12 to 18 months
Fire Head of Sales
6. FAIL!
Typical Startup Outcome
1. Idea!
2. Technical Co-Founders
3. Raise Money
4. Build Product
5. While( Cash Remains )
Hire Head of Sales
<stuff happens>
Wait 12 to 18 months
Fire Head of Sales
6. FAIL!
Building Sales Orgs in 3 Phases
Proving Product Value
Understanding the Sale
Scaling the organization
Essence of Phase 1
Proving a Market Exists for your
Product and People will Buy It
Phase 1 -> Challenge
The Product
Probably Really,
Really Stinks
Phase 1 -> Implication
Customers are buying into your
vision more than your product
Phase 1 Best Practices
• Lean Startup Concepts
– Getting to Minimum Viable Product
• Founder selling of the vision
• Talking to BUYERS and USERS
– all the personas in the value chain
• No Free Stuff: Prove Value, Test Pricing
Stack Overflow Careers
(Proving Product Value)
Proving Product Value
Understanding the Sale
Scaling the organization
Phase 2 Goal
Multiple Sales Reps
Closing Deals on
their Own
Common Phase 2 Problem
FOUNDER: “I can close customers
myself without any problem, but the
reps I’ve hired can’t close the deals on
their own”
Common Phase 2 Problem
SALES REP: “I can’t close customer X without
feature Y”
and
SALES REP: “If I had Feature A, then I could sell
way more”
Add More Features!!?
Best Way to Increase Sales???
No, it’s cheating because it
expands your addressable
market, it doesn’t increase
actual rate of penetration.
Understanding The Sale
• <Web Direct> || <Use Humans>
• <Inbound Leads> || <Outbound Prospecting>
• <Split Sale> || <Full Stack>
Phase 2 Best Practices
• You product will always suck to some extent
– Admit it to the Sales Reps, Sell what you have
• Get to at least Three Sales Reps as fast as possible
– You want multiple petri dishes
• Aggressive Compensation Plan
– Want successful reps making a ton of money
• Fight all urges to use discounts to close deals
• Sales Manager not Needed yet
– But a good idea to be looking!!
Proving Product Value
Understanding the Sale
Scaling the organization
Phase 3 Goal
Predictable
Revenue that is
Rapidly Scaling
Phase 3 Bad News
• Nature of Sales is Changing Rapidly
• Classic Management Methods Failing
• Experience != Expertise
• Poor at Predictions of Outcomes
• Seemingly More Art than Science
• No Magical Processes to Follow
Phase 3 Bad News
• Nature of Sales is Changing Rapidly
• Classic Management Methods Failing
• Experience != Expertise
• Poor at Predictions of Outcomes
• Seemingly More Art than Science
• No Magical Processes to Follow
Phase 3 Insight
Good Sales
Management
approaches parallel
Good Software
Development
approaches!!
Properties of
Successful
Software
Development
Understand Performance != Results
Software Development
• Discovering, Developing and
Finalizing Requirements
• System Architecture, Design and
Code Construction
• Quality Control including effective
testing and validation
• Task Estimation and Project
Management
• Deployment and Ongoing
Maintenance
A bunch of Separable
Skills that individuals
and the team must be
process capable of
Phase 3: Skills Development
Software Development
• Discovering, Developing and
Finalizing Requirements
• System Architecture, Design and
Code Construction
• Quality Control including effective
testing and validation
• Task Estimation and Project
Management
• Deployment and Ongoing
Maintenance
• Team Morale and Cadence
Sales Development
• Prospecting
• Questioning
• Proposal Development and
Pitching
• Objection Handling
• Closing Skills
• Negotiation
• Time and Pipeline Management
• Team Morale and Cadence
Cadence and Team Morale
• Bottom Up Schedule Estimates
• Strive for Continuous and Steady Output
– Team Goals but No death marches
• Using Peer and Social Pressure vs. Edicts
– Setting Cultural Norms and Expectations
• Compensation Fairness
• Merit not tenure based Advancement
“Full Stack” Sales Rep
Each Rep runs their Own Small Business:
• End to End ownership of the relationships
• Sets their Own Forecasts
• Picks their Own Accounts
• No scripts, No quotas
• Works under shared best practices
• Supported by Team Leader and Sales Manager
Sales Manager
• Primary Responsibility is Skills Development
• Parallel to the Engineering Manager
• Removes Operational Barriers
– Helps define and build common infrastructure
• Works with a Longer Term Horizon
– More Quarter to Quarter than Day to Day
Team Leads
• Drives Cadence and Morale of the Team
• Parallel to the Technical Team Dev Leads
• Walking Personification of Ideal Sales Rep
• Natural Leaders that enjoy Mentoring
• Player and a Coach -> Carries full account load
• Eyes and Ears for Sales Management
– Spot treatments not skills development
Phase 3 Role Separation
Team Leaders => Track Racing Pit Crew
Sales Management => Garage Mechanics
SCRUM Sprint Based Process
• Team Based & driven by the Team Leads
• Operated as Joint Retrospective and Standup
• Monthly Forecasting Cycle into Four Sprints
• Reinforces Team Work and Shared Best Practices
• Friendly competition between Teams and Offices
Phase 3 Best Practices
• First Phase with Professional Sales Manager(s)
• Separate Performance from Results
• Developing Suites of Skills in Each Rep
• Empower the Reps and Teams to Self Manage
• Each rep is running their own little business
• Autonomy and empowerment is the name of the
game
Three Things You Can Do Tomorrow
• Proving Value: Make sure you understand the
niche you are serving and stay focused on that
• Validate Your Understanding of Your Pitch by
showing that others can do it as well as you
• Forecast from the Bottom Up: Top down
projections are just wishful thinking
Thank you!!!
talljeff@stackoverflow.com
@inscitekjeff
Blog: DevelopingSales.com

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Jeff Szczepanski Pipeline Summit

  • 1. How a Developer Builds a Sales Team (Scaling Sales the Agile Way) Jeff Szczepanski, COO
  • 2. What is the Objective?
  • 3. Objective Predictable Revenue that is Scaling Fast (Building a Billion Dollar Company)
  • 4. What is the Plan?
  • 5. Typical Startup Plan 1.Idea! 2.Technical Co-Founders 3.Raise Money 4.Build Great Product 5.Hire Head of Sales ie: ‘Needz Sales’ 6.Profit!!
  • 6. Typical Startup Outcome 1. Idea! 2. Technical Co-Founders 3. Raise Money 4. Build Product 5. While( Cash Remains ) Hire Head of Sales <some stuff happens> Wait 12 to 18 months Fire Head of Sales 6. FAIL!
  • 7. Typical Startup Outcome 1. Idea! 2. Technical Co-Founders 3. Raise Money 4. Build Product 5. While( Cash Remains ) Hire Head of Sales <stuff happens> Wait 12 to 18 months Fire Head of Sales 6. FAIL!
  • 8. Building Sales Orgs in 3 Phases Proving Product Value Understanding the Sale Scaling the organization
  • 9. Essence of Phase 1 Proving a Market Exists for your Product and People will Buy It
  • 10. Phase 1 -> Challenge The Product Probably Really, Really Stinks
  • 11. Phase 1 -> Implication Customers are buying into your vision more than your product
  • 12. Phase 1 Best Practices • Lean Startup Concepts – Getting to Minimum Viable Product • Founder selling of the vision • Talking to BUYERS and USERS – all the personas in the value chain • No Free Stuff: Prove Value, Test Pricing
  • 14. Proving Product Value Understanding the Sale Scaling the organization
  • 15. Phase 2 Goal Multiple Sales Reps Closing Deals on their Own
  • 16. Common Phase 2 Problem FOUNDER: “I can close customers myself without any problem, but the reps I’ve hired can’t close the deals on their own”
  • 17. Common Phase 2 Problem SALES REP: “I can’t close customer X without feature Y” and SALES REP: “If I had Feature A, then I could sell way more”
  • 18. Add More Features!!? Best Way to Increase Sales??? No, it’s cheating because it expands your addressable market, it doesn’t increase actual rate of penetration.
  • 19. Understanding The Sale • <Web Direct> || <Use Humans> • <Inbound Leads> || <Outbound Prospecting> • <Split Sale> || <Full Stack>
  • 20. Phase 2 Best Practices • You product will always suck to some extent – Admit it to the Sales Reps, Sell what you have • Get to at least Three Sales Reps as fast as possible – You want multiple petri dishes • Aggressive Compensation Plan – Want successful reps making a ton of money • Fight all urges to use discounts to close deals • Sales Manager not Needed yet – But a good idea to be looking!!
  • 21. Proving Product Value Understanding the Sale Scaling the organization
  • 22. Phase 3 Goal Predictable Revenue that is Rapidly Scaling
  • 23. Phase 3 Bad News • Nature of Sales is Changing Rapidly • Classic Management Methods Failing • Experience != Expertise • Poor at Predictions of Outcomes • Seemingly More Art than Science • No Magical Processes to Follow
  • 24. Phase 3 Bad News • Nature of Sales is Changing Rapidly • Classic Management Methods Failing • Experience != Expertise • Poor at Predictions of Outcomes • Seemingly More Art than Science • No Magical Processes to Follow
  • 25. Phase 3 Insight Good Sales Management approaches parallel Good Software Development approaches!!
  • 27. Understand Performance != Results Software Development • Discovering, Developing and Finalizing Requirements • System Architecture, Design and Code Construction • Quality Control including effective testing and validation • Task Estimation and Project Management • Deployment and Ongoing Maintenance A bunch of Separable Skills that individuals and the team must be process capable of
  • 28. Phase 3: Skills Development Software Development • Discovering, Developing and Finalizing Requirements • System Architecture, Design and Code Construction • Quality Control including effective testing and validation • Task Estimation and Project Management • Deployment and Ongoing Maintenance • Team Morale and Cadence Sales Development • Prospecting • Questioning • Proposal Development and Pitching • Objection Handling • Closing Skills • Negotiation • Time and Pipeline Management • Team Morale and Cadence
  • 29. Cadence and Team Morale • Bottom Up Schedule Estimates • Strive for Continuous and Steady Output – Team Goals but No death marches • Using Peer and Social Pressure vs. Edicts – Setting Cultural Norms and Expectations • Compensation Fairness • Merit not tenure based Advancement
  • 30. “Full Stack” Sales Rep Each Rep runs their Own Small Business: • End to End ownership of the relationships • Sets their Own Forecasts • Picks their Own Accounts • No scripts, No quotas • Works under shared best practices • Supported by Team Leader and Sales Manager
  • 31. Sales Manager • Primary Responsibility is Skills Development • Parallel to the Engineering Manager • Removes Operational Barriers – Helps define and build common infrastructure • Works with a Longer Term Horizon – More Quarter to Quarter than Day to Day
  • 32. Team Leads • Drives Cadence and Morale of the Team • Parallel to the Technical Team Dev Leads • Walking Personification of Ideal Sales Rep • Natural Leaders that enjoy Mentoring • Player and a Coach -> Carries full account load • Eyes and Ears for Sales Management – Spot treatments not skills development
  • 33. Phase 3 Role Separation Team Leaders => Track Racing Pit Crew Sales Management => Garage Mechanics
  • 34. SCRUM Sprint Based Process • Team Based & driven by the Team Leads • Operated as Joint Retrospective and Standup • Monthly Forecasting Cycle into Four Sprints • Reinforces Team Work and Shared Best Practices • Friendly competition between Teams and Offices
  • 35. Phase 3 Best Practices • First Phase with Professional Sales Manager(s) • Separate Performance from Results • Developing Suites of Skills in Each Rep • Empower the Reps and Teams to Self Manage • Each rep is running their own little business • Autonomy and empowerment is the name of the game
  • 36. Three Things You Can Do Tomorrow • Proving Value: Make sure you understand the niche you are serving and stay focused on that • Validate Your Understanding of Your Pitch by showing that others can do it as well as you • Forecast from the Bottom Up: Top down projections are just wishful thinking

Editor's Notes

  1. Come to terms with it and admit it. You product sucks here. Hardly anybody really wants to buy it. This is OK. You have to start somewhere and again this is what MVP and product market fit is all about. You are finding yourself and converting the core of what is hopefully a really good idea into a product people hopefully want to buy. But there is important implications to selling here. (And yes, you should be selling!!)
  2. Phase Two I call, Understanding Your pitch. This phase is about translating the vision into a series of pitch angles that resonate with your prospects and tell story that paints your products in a favorable and desirable light. Thing of it a customer’s “choose your own adventure” where all paths ideally lead to a purchase.
  3. Phase 2 is when you are allowed to start hiring sales reps. The goal here is to end up with multiple sales reps selling your product and successfully closing deals on their own. Note that I have said nothing here about sales management yet. Phase 2 is not yet about professional sales management. It’s about giving the reps their own autonomy, and tooled with the ability to sell effectively.
  4. Predictable Revenue that is scaling. The emphasis here is on the predictability and consistency, not unlike what you would want to see your software development team doing.
  5. This sounds a lot like software development. Yes, due to this changing nature of sales, I’m arguing that the creative process of developing sales with clients isn’t a lot different from a process perspective at the creative process of developing software. This raises a somewhat provocative question….
  6. Ok, we’re saying modern software development and modern sales development have a parallel nature. What are the practical and actionable implications of this? For that, we have to explore a bit of what makes good software development.
  7. From a management and leadership perspective, you have to understand that Performance and Results are not the same thing. You can’t just look at the desired outcomes and drive it by those numbers. For software you can’t look at things like “lines of code generated per day” or even “bugs found per day” as useful management metrics. In sales, this is a huge pitfall because things like phone calls made, emails sent and revenue generated are very easy to measure, but it doesn’t really mean you know what is going into the those activities and the difference between quality and quantity. You have to be looking at the underlying skills. <WORK THROUGH SLIDE>
  8. The parallel in sales to all those software skills, is these selling skills. <WORK THROUGH THE SLIDE> The people on the team have to be equipped with tools and skills to do these things autonomously.
  9. The human side of the equation is also really important. To a large extent both sales and coding is a repetitive process….rebuilding or leverage pre-existing techniques. Therefore, morale and cadence issues is huge piece of the equation. <WORK THROUGH SLIDE>
  10. Breaking it down further and applying the software developer role model to the sale rep role mode, you have to think about it like each rep is managing their own business, just like a coder develops and maintains their own code modules.
  11. The sales managers. These are extremely important role. In many ways the ideal sales manager is more of coach and psychologist that a manager. Their core function should be skills development. Again, with tools and skills, getting each rep to be self-sufficient at managing their pipelines. <SLIDE>
  12. <SLIDE>
  13. The teams and their day to day operations and pipeline management is run based directly off the SCRUM software development methodologies. <WORK THROUGH THE SLIDE>