Startup CXO

Startup CXO

by Matt Blumberg, Peter M. Birkeland, Scott Dorsey
Released June 2021
Publisher(s): Wiley
ISBN: 9781119772576

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Book description

One of the greatest challenges for startup teams is scaling because usually there's not a blueprint to follow, people are learning their function as they go, and everyone is wearing multiple hats. There can be lots of trial and error, lots of missteps, and lots of valuable time and money squandered as companies scale. Matt Blumberg and his team understand the scaling challenges—they've been there, and it took them nearly 20 years to scale and achieve a successful exit.  Along the way they learned what worked and what didn’t work, and they share their lessons learned in Startup CXO.

Unlike other business books, Startup CXO is designed to help each functional leader understand how their function scales, what to anticipate as they scale, and what things to avoid. Beyond providing function-specific advice, tools, and tactics, Startup CXO is a resource for each team member to learn about the other functions, understand other functional challenges, and get greater clarity on how to collaborate effectively with the other functional leads.

CEOs, Board members, and investors have a book they can consult to pinpoint areas of weakness and learn how to turn those into strengths. Startup CXO has in-depth chapters covering the nine most common functions in startups: finance, people, marketing, sales, customers, business development, product, operations, and privacy. Each functional section has a "CEO to CEO Advice" summary from Blumberg on what great looks like for that CXO, signs your CXO isn't scaling, and how to engage with your CXO.

Startup CXO also has a section on the future of executive work, fractional and interim roles. Written by leading practitioners in the newly emergent fractional executive world, each function is covered with useful tips on how to be a successful fractional executive as well as what to look for and how to manage fractional executives.

Startup CXO is an amazing resource for CEOs but also for functional leaders and professionals at any stage of their career."
—Scott Dorsey, Managing Partner, High Alpha

Table of contents

  1. Cover
  2. Title Page
  3. Copyright
  4. Dedication
  5. Foreword
  6. Part One: Introduction
    1. Introduction
    2. Chapter 1: The Nature of a CXO's Role
    3. Chapter 2: Scaling a CXO
  7. Part Two: Finance and Administration
    1. Chief Financial Officer
    2. Chapter 3: In the Beginning: Laying the CFO Foundation
    3. Chapter 4: Fundraising
      1. Preparing for a Fundraising Event
      2. The Pitch Deck
    4. Chapter 5: Size of Opportunity
    5. Chapter 6: Financial Plan
    6. Chapter 7: Unit Economics and KPIs
    7. Chapter 8: Investor Ecosystem Research
    8. Chapter 9: Pricing and Valuation
    9. Chapter 10: Due Diligence and Corporate Documentation
    10. Chapter 11: Using External Counsel
    11. Chapter 12: Operational Accounting
      1. Accounting Rules Implementation
    12. Chapter 13: Treasury and Cash Management
    13. Chapter 14: Building an In‐House Accounting Team
    14. Chapter 15: International Operations
    15. Chapter 16: Strategic Finance
      1. Sales
      2. Service
      3. Marketing
      4. Legal
    16. Chapter 17: Other Areas to Partner With
    17. Chapter 18: High Impact Areas for the Startup CFO as Partner
      1. Interest to Order: Order to Cash
    18. Chapter 19: Board and Shareholder Management
    19. Chapter 20: Equity
      1. Equity Management
      2. Secondary/Tender Transactions
      3. 409a Valuations
    20. Chapter 21: Mergers and Acquisitions (M&A)
      1. Buy‐Side
      2. Sell‐Side
    21. Chapter 22: Bonus Section: What We Used for Our Internal Systems When We Started Bolster
      1. Selected Systems
    22. Chapter 23: CEO‐to‐CEO Advice About the Finance Role
      1. Signs It's Time to Hire Your First CFO
      2. When a Fractional CFO Might Be Enough
      3. What Does Great Look Like in a CFO?
      4. Signs Your CFO Isn't Scaling
      5. How I Engage with the CFO
  8. Part Three: People and Human Resources
    1. Chief People Officer
    2. Chapter 24: Values and Culture
    3. Chapter 25: Diversity, Equity, and Inclusion (DE&I)
    4. Chapter 26: Building Your Team
    5. Chapter 27: Organizational Design and Operating Systems
    6. Chapter 28: Team Development
    7. Chapter 29: Leadership Development
    8. Chapter 30: Talent and Performance Management
    9. Chapter 31: Career Pathing
    10. Chapter 32: Role‐Specific Learning and Development
    11. Chapter 33: Employee Engagement
    12. Chapter 34: Rewards and Recognition
    13. Chapter 35: Reductions in Force
    14. Chapter 36: Recruiting
    15. Chapter 37: Onboarding
    16. Chapter 38: Compensation
      1. On Decision Making
    17. Chapter 39: People Operations
      1. Processes
    18. Chapter 40: Systems
      1. Conclusion
    19. Chapter 41: CEO‐to‐CEO Advice About the People/HR Role
      1. Signs It's Time to Hire Your First Chief People Officer
      2. When a Fractional Chief People Officer Might Be Enough
      3. What Does Great Look Like in a Chief People Officer?
      4. Signs Your Chief People Officer Isn't Scaling
      5. How I Engage with the Chief People Officer
  9. Part Four: Marketing
    1. Chief Marketing Officer
      1. What Is Marketing, Really?
    2. Chapter 42: Where to Start
      1. Building and Maintaining a Brand
    3. Chapter 43: Generating Demand for Sales
      1. Market Research
      2. Competitive Intelligence
      3. Technology
      4. Metric Definition
    4. Chapter 44: Supporting the Company Culture
      1. Recruitment Marketing
      2. Internal Communications
      3. Employee Engagement
    5. Chapter 45: Breaking Down Marketing's Functions
      1. Brand
      2. Digital
    6. Chapter 46: Events
      1. Types of Events
      2. Event Planning
      3. Partnering with Sales
      4. Pre‐Event
      5. Event Execution
      6. Post‐Event
      7. Using Data
    7. Chapter 47: Content and Communications
      1. Public Relations
      2. Content Creation
      3. Gated Versus Ungated?
    8. Chapter 48: Product Marketing
      1. Deliver
      2. Create
      3. Analyst Relations
      4. Enable
    9. Chapter 49: Marketing Operations
      1. Technology
      2. Process
      3. Measurement
      4. Strategic Planning
      5. When to Start Marketing Operations
    10. Chapter 50: Sales Development
      1. Sales or Marketing?
      2. Leadership
      3. Where to Start
      4. A Note on Working with Agencies
    11. Chapter 51: Marketing as a Partner/Collaborating with the Rest of the C‐suite
    12. Chapter 52: Building a Marketing Machine (Scaleup)
      1. Growing Your Team
      2. Execute Across Channels
      3. Broaden Your Reach
      4. Final Thoughts
    13. Chapter 53: CEO‐to‐CEO Advice About the Marketing Role
      1. Signs It's Time to Hire Your First CMO
      2. When a Fractional CMO Might Be Enough
      3. What Does Great Look Like in a CMO?
      4. Signs Your CMO Isn't Scaling
      5. How I Engage with the CMO
  10. Part Five: Sales
    1. Chief Revenue Officer
    2. Chapter 54: In the Beginning: From Prospect to Customer
    3. Chapter 55: Hiring the Right People
    4. Chapter 56: Profile of Successful Salespeople
    5. Chapter 57: Some Myth Busting
    6. Chapter 58: Compensating Sales Team Members
      1. Incentive Compensation Revisited
    7. Chapter 59: Pipeline
    8. Chapter 60: Scaling the Sales Organization
    9. Chapter 61: Scaling Your Team Through Culture
    10. Chapter 62: Scaling Sales Process and Methodology
    11. Chapter 63: Scaling the Operating System
    12. Chapter 64: Marketing Alignment
    13. Chapter 65: Market Assessment and Alignment
    14. Chapter 66: Expanding Distribution Channels
    15. Chapter 67: Geographic Expansion
    16. Chapter 68: Pricing and Packaging
      1. Pricing
      2. Packaging
      3. Final Thoughts
    17. Chapter 69: CEO‐to‐CEO Advice About the Sales Role
      1. Signs It's Time to Hire Your First CRO
      2. When a Fractional CRO Might Be Enough
      3. What Does Great Look Like in a CRO?
      4. Signs Your CRO Isn't Scaling
      5. How I Engage with the CRO
  11. Part Six: Business/Corporate Development
    1. Chief Business Development Officer
      1. To Create a CBDO or Not?
    2. Chapter 70: How to Make the Biggest Impact as a CBDO
    3. Chapter 71: Building Your Influence Internally
    4. Chapter 72: Building Your Influence Externally
    5. Chapter 73: Where Internal and External Meet: Your Relationship with Your CEO
    6. Chapter 74: Influence Meets Operating System
    7. Chapter 75: Develop External Trust for the Company
    8. Chapter 76: Build Your Influence in Strategy
    9. Chapter 77: Building Your Influence in Business Development
      1. Outbound
      2. Inbound
    10. Chapter 78: When Things Go Wrong in a Partnership…and They Will
    11. Chapter 79: Geographic Expansion
    12. Chapter 80: M&A: Buy Side
    13. Chapter 81: M&A: Sell Side
      1. Final Thoughts
    14. Chapter 82: CEO‐to‐CEO Advice About the Business/Corporate Development Role
      1. Signs It's Time to Hire Your First CBDO
      2. When a Fractional CBDO Might Be Enough
      3. What Does Great Look Like in a CBDO?
      4. Signs Your CBDO Isn't Scaling
      5. How I Engage with the CBDO
  12. Part Seven: Customer Success/Account Management
    1. Chief Customer Officer
      1. Welcome to the New World
    2. Chapter 83: Five Misperceptions
    3. Chapter 84: Startup Customer Success Organization
    4. Chapter 85: Scaling the Service Organization
    5. Chapter 86: Timing: When to Hire Your Team
    6. Chapter 87: Customer Segmentation and Journey
      1. Segment Your Customers
      2. Set an Appropriate Customer Experience for Each Segment
      3. Coordinate with Sales
    7. Chapter 88: Understanding Customers
    8. Chapter 89: Understanding Customers Through Metrics
      1. Onboarding Phase Metrics
      2. Activation Phase Metrics
      3. Use Phase Metrics
      4. Renewal
    9. Chapter 90: Foundations of a Great Customer Service Organization
      1. Data
      2. Technology
      3. People
    10. Chapter 91: Building an Effective Team
    11. Chapter 92: Partnering with the Organization
    12. Chapter 93: Five Eternal Questions
      1. 1 How Should I Structure Variable Compensation for the Customer Success Team?
      2. 2 Who Does the Upsell?
      3. 3 Doesn't the Customer Service Organization Own Churn?
      4. 4 Shouldn't We Charge for Onboarding Services?
      5. 5 Where Does Customer Advocacy Live?
      6. Summary
    13. Chapter 94: CEO‐to‐CEO Advice About the Customer Success Role
      1. Signs It's Time to Hire Your First CCO
      2. When a Fractional CCO Might Be Enough
      3. What Does Great Look Like in a CCO?
      4. Signs Your CCO Isn't Scaling
      5. How I Engage with the CCO
  13. Part Eight: Product and Engineering
    1. Chief Product Officer and Chief Technology Officer
    2. Chapter 95: The Product Development Leaders
    3. Chapter 96: Product Development Culture
      1. Types of Development Cultures
    4. Chapter 97: Technical Strategy: Proportional Engineering Investment and Managing Technical Debt
    5. Chapter 98: Shifting to a New Development Culture
      1. Things to Consider
    6. Chapter 99: Starting Things
      1. Things to Consider
    7. Chapter 100: Hiring Product Development Team Members
      1. Interviewing
      2. Onboarding
      3. Bootcamps
    8. Chapter 101: Increasing the Funnel and Building Diverse Teams
    9. Chapter 102: Retaining and Career Pathing People
    10. Chapter 103: Hiring and Growing Leaders
      1. Other Things to Consider
    11. Chapter 104: Organizing, Collaborating with, and Motivating Effective Teams
      1. Example 1: Quality
      2. Example 2: Unified Product Development Organization
      3. Example 3: Impedance Mismatch
      4. Things to Consider
    12. Chapter 105: Due Diligence and Lessons Learned from a Sale Process
      1. People
      2. Team
      3. Product
      4. System Overview
      5. Privacy/Security
      6. IP and Legal Risks
      7. Costs
      8. Risk Assessment
    13. Chapter 106: Selling Your Company: Preparation
      1. Preparation
    14. Chapter 107: Selling Your Company: Telling the Story
      1. Conclusion
    15. Chapter 108: CEO‐to‐CEO Advice About the Product/Engineering Role
      1. Signs It's Time to Hire Your First Chief Product Officer
      2. When a Fractional Chief Product Officer Might Be Enough
      3. Signs It's Time to Hire Your First Chief Technology Officer
      4. When a Fractional Chief Technology Officer Might Be Enough
      5. What Does Great Look Like in a Chief Product or Technology Officer?
      6. Signs Your Chief Product or Technology Officer Isn't Scaling
      7. How I Engage with the Chief Product or Technology Officer
  14. Part Nine: Privacy
    1. Chief Privacy Officer
      1. The Rise of the Privacy Officer
    2. Chapter 109: The Role of Privacy Officer
    3. Chapter 110: Privacy Advice for Startups
    4. Chapter 111: Legal Documents
      1. Privacy Policy
      2. Internal Privacy Policy
      3. Terms of Service
    5. Chapter 112: The European Union
    6. Chapter 113: Data Mapping
    7. Chapter 114: Data Breach
    8. Chapter 115: Least Privileged Access
    9. Chapter 116: Employee Training Engagement
    10. Chapter 117: Building Your Privacy Team in a Startup
    11. Chapter 118: Building Your Privacy Team as You Scaleup
    12. Chapter 119: Certifications
    13. Chapter 120: Assessments
      1. Final Thoughts
    14. Chapter 121: CEO‐to‐CEO Advice About the Privacy Role
      1. Signs It's Time to Hire Your First CPO
      2. When a Fractional Chief Privacy Officer Might Be Enough
      3. What Does Great Look Like in a Chief Privacy Officer?
      4. Signs Your CPO Isn't Scaling
      5. How I Engage with the CPO
  15. Part Ten: Operations
    1. Chief Operating Officer
      1. Types of COOs
      2. A Few Common Areas for the COO
    2. Chapter 122: CEO‐to‐CEO Advice About the Operating Role
      1. Complexity or Crutch?
  16. Part Eleven: The Future of Executive Work
    1. Chapter 123: The Future of Executive Work
      1. Welcome to the Executive Gig Economy
    2. Chapter 124: Fractional Chief Financial Officer
      1. The Need
      2. The Structure
      3. The Role
      4. The Skills
      5. The Exit
    3. Chapter 125: Fractional Chief People Officer
      1. Fractional HR Tasks
      2. Startup or Established?
      3. Transitions
      4. Qualities of a Fractional HR Person
    4. Chapter 126: Fractional Chief Marketing Officer
      1. Fractional Opportunities for CMOs
      2. Qualities of a Fractional CMO
      3. Fractional Opportunities for Companies
    5. Chapter 127: Fractional Chief Revenue Officer
      1. Becoming a Fractional Executive
      2. Finding Fractional Roles
      3. Cautionary Advice
    6. Chapter 128: Fractional Chief Revenue Officer
      1. Qualities of a Fractional CRO
      2. What to Expect as a Fractional CRO
      3. The Good Part
    7. Chapter 129: Fractional Chief Business Development Officer
      1. Alignment
      2. Objectives
      3. Trust
      4. Passion
    8. Chapter 130: Fractional Chief Customer Officer
      1. Things to Figure Out Quickly
      2. Should You Pursue a Fractional Role?
      3. Why Companies Need Fractional Executives
    9. Chapter 131: Fractional Chief Product/Technology Officer
      1. Getting Started in a Fractional Product Role
      2. What Does a Fractional Product Person Do?
      3. Advice for Companies
      4. Final Thought
    10. Chapter 132: Fractional Chief Privacy Officer
      1. Qualities of a Fractional Privacy Officer
      2. What a Fractional Privacy Officer Does
      3. Advice for Companies
  17. Conclusion
  18. Epilogue
  19. References
  20. Acknowledgments
  21. About the Authors
    1. Contributors
  22. Index
  23. End User License Agreement

Product information

  • Title: Startup CXO
  • Author(s): Matt Blumberg, Peter M. Birkeland, Scott Dorsey
  • Release date: June 2021
  • Publisher(s): Wiley
  • ISBN: 9781119772576