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
