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
Foreword xvii
Part One: Introduction 1
Matt Blumberg
Introduction 2
Chapter 1: The Nature of a CXO's Role 9
Chapter 2: Scaling a CXO 12
Part Two: Finance and Administration 15
Jack Sinclair
Chief Financial Officer 16
Chapter 3: In the Beginning: Laying the CFO Foundation 19
Chapter 4: Fundraising 22
Chapter 5: Size of Opportunity 25
Chapter 6: Financial Plan 27
Chapter 7: Unit Economics and KPIs 30
Chapter 8: Investor Ecosystem Research 32
Chapter 9: Pricing and Valuation 34
Chapter 10: Due Diligence and Corporate Documentation 37
Chapter 11: Using External Counsel 40
Chapter 12: Operational Accounting 42
Chapter 13: Treasury and Cash Management 49
Chapter 14: Building an In-House Accounting Team 52
Chapter 15: International Operations 55
Chapter 16: Strategic Finance 58
Chapter 17: Other Areas to Partner With 67
Chapter 18: High Impact Areas for the Startup CFO as Partner 71
Chapter 19: Board and Shareholder Management 77
Chapter 20: Equity 80
Chapter 21: Mergers and Acquisitions (M&A) 85
Chapter 22: Bonus Section: WhatWe Used for Our Internal Systems WhenWe Started Bolster 91
Chapter 23: CEO-to-CEO Advice About the Finance Role 97
Matt Blumberg
Part Three: People and Human Resources 101
Cathy Hawley
Chief People Officer 102
Chapter 24: Values and Culture 105
Chapter 25: Diversity, Equity, and Inclusion (DE&I) 111
Chapter 26: Building Your Team 113
Chapter 27: Organizational Design and Operating Systems 118
Chapter 28: Team Development 124
Chapter 29: Leadership Development 127
Chapter 30: Talent and Performance Management 130
Chapter 31: Career Pathing 132
Chapter 32: Role-Specific Learning and Development 134
Chapter 33: Employee Engagement 136
Chapter 34: Rewards and Recognition 138
Chapter 35: Reductions in Force 140
Chapter 36: Recruiting 142
Chapter 37: Onboarding 149
Chapter 38: Compensation 152
Chapter 39: People Operations 154
Chapter 40: Systems 164
Chapter 41: CEO-to-CEO Advice About the People/HR Role 167
Matt Blumberg
Part Four: Marketing 173
Nick Badgett and Holly Enneking
Chief Marketing Officer 174
Chapter 42: Where to Start 177
Chapter 43: Generating Demand for Sales 181
Chapter 44: Supporting the Company Culture 186
Chapter 45: Breaking Down Marketing’s Functions 191
Chapter 46: Events 204
Chapter 47: Content and Communications 212
Chapter 48: Product Marketing 218
Chapter 49: Marketing Operations 223
Chapter 50: Sales Development 226
Chapter 51: Marketing as a Partner/Collaborating with the Rest of the C-suite 233
Chapter 52: Building a Marketing Machine (Scaleup) 236
Chapter 53: CEO-to-CEO Advice About the Marketing Role 243
Matt Blumberg
Part Five: Sales 249
Anita Absey
Chief Revenue Officer 250
Chapter 54: In the Beginning: From Prospect to Customer 251
Chapter 55: Hiring the Right People 254
Chapter 56: Profile of Successful Salespeople 257
Chapter 57: Some Myth Busting 260
Chapter 58: Compensating Sales Team Members 262
Chapter 59: Pipeline 266
Chapter 60: Scaling the Sales Organization 268
Chapter 61: Scaling Your Team Through Culture 271
Chapter 62: Scaling Sales Process and Methodology 276
Chapter 63: Scaling the Operating System 279
Chapter 64: Marketing Alignment 282
Chapter 65: Market Assessment and Alignment 286
Chapter 66: Expanding Distribution Channels 288
Chapter 67: Geographic Expansion 291
Chapter 68: Pricing and Packaging 294
Chapter 69: CEO-to-CEO Advice About the Sales Role 300
Matt Blumberg
Part Six: Business/Corporate Development 305
Ken Takahashi
Chief Business Development Officer 306
Chapter 70: How to Make the Biggest Impact as a CBDO 311
Chapter 71: Building Your Influence Internally 314
Chapter 72: Building Your Influence Externally 318
Chapter 73: Where Internal and External Meet: Your Relationship with Your CEO 323
Chapter 74: Influence Meets Operating System 325
Chapter 75: Develop External Trust for the Company 327
Chapter 76: Build Your Influence in Strategy 329
Chapter 77: Building Your Influence in Business Development 330
Chapter 78: When Things GoWrong in a Partnership…and They Will 335
Chapter 79: Geographic Expansion 338
Chapter 80: M&A: Buy Side 341
Chapter 81: M&A: Sell Side 344
Chapter 82: CEO-to-CEO Advice About the Business/Corporate Development Role 348
Matt Blumberg
Part Seven: Customer Success/Account Management 353
George Bilbrey
Chief Customer Officer 354
Chapter 83: Five Misperceptions 357
Chapter 84: Startup Customer Success Organization 360
Chapter 85: Scaling the Service Organization 362
Chapter 86: Timing: When to Hire Your Team 366
Chapter 87: Customer Segmentation and Journey 368
Chapter 88: Understanding Customers 372
Chapter 89: Understanding Customers Through Metrics 374
Chapter 90: Foundations of a Great Customer Service Organization 379
Chapter 91: Building an Effective Team 385
Chapter 92: Partnering with the Organization 387
Chapter 93: Five Eternal Questions 391
Chapter 94: CEO-to-CEO Advice About the Customer Success Role 396
Matt Blumberg
Part Eight: Product and Engineering 401
Shawn Nussbaum
Chief Product Officer and Chief Technology Officer 402
Chapter 95: The Product Development Leaders 405
Chapter 96: Product Development Culture 412
Chapter 97: Technical Strategy: Proportional Engineering Investment and Managing Technical Debt 416
Chapter 98: Shifting to a New Development Culture 424
Chapter 99: Starting Things 427
Chapter 100: Hiring Product Development Team Members 434
Chapter 101: Increasing the Funnel and Building Diverse Teams 442
Chapter 102: Retaining and Career Pathing People 446
Chapter 103: Hiring and Growing Leaders 449
Chapter 104: Organizing, Collaborating with, and Motivating Effective Teams 455
Chapter 105: Due Diligence and Lessons Learned from a Sale Process 468
Chapter 106: Selling Your Company: Preparation 475
Chapter 107: Selling Your Company: Telling the Story 479
Chapter 108: CEO-to-CEO Advice About the Product/Engineering Role 482
Matt Blumberg
Part Nine: Privacy 487
Dennis Dayman
Chief Privacy Officer 488
Chapter 109: The Role of Privacy Officer 491
Chapter 110: Privacy Advice for Startups 494
Chapter 111: Legal Documents 500
Chapter 112: The European Union 505
Chapter 113: Data Mapping 507
Chapter 114: Data Breach 510
Chapter 115: Least Privileged Access 515
Chapter 116: Employee Training Engagement 519
Chapter 117: Building Your Privacy Team in a Startup 522
Chapter 118: Building Your Privacy Team as You Scaleup 525
Chapter 119: Certifications 527
Chapter 120: Assessments 529
Chapter 121: CEO-to-CEO Advice About the Privacy Role 536
Matt Blumberg
Part Ten: Operations 541
Jack Sinclair
Chief Operating Officer 542
Chapter 122: CEO-to-CEO Advice About the Operating Role 549
Matt Blumberg
Part Eleven: The Future of ExecutiveWork 551
Chapter 123: The Future of ExecutiveWork 553
Matt Blumberg
Chapter 124: Fractional Chief Financial Officer 556
John McCarthy
Chapter 125: Fractional Chief People Officer 562
Courtney Graeber
Chapter 126: Fractional Chief Marketing Officer 567
Scott Kabat
Chapter 127: Fractional Chief Revenue Officer 571
B.J. Bushur
Chapter 128: Fractional Chief Revenue Officer 576
Sherri Sklar
Chapter 129: Fractional Chief Business Development Officer 580
Jon Guttenberg
Chapter 130: Fractional Chief Customer Officer 586
Amy Mustoe
Chapter 131: Fractional Chief Product/Technology Officer 590
Drew Dillon
Chapter 132: Fractional Chief Privacy Officer 594
Teresa Troester-Falk
Conclusion 599
Epilogue 601
Pete Birkeland
References 603
Acknowledgments 604
About the Authors 606
Index 613
