INDEX
- A
- Accelerator, mentors (joining), 273
- Accountant, hiring, 80
- Adsit, Dennis, 95
- Affinity organizations, 275–276
- After actions (retrospectives), 187
- Alliance, The (Hoffman/Casnocha/Yeh), 148
- Altman, Jack, 97
- Ammons, Jeff, 62–63, 119–120
- Annual contract value (ACV), company sale, 98
- Annual Recurring Revenue (ARR), 044, 48, 53, 98, 116, 251
- Annual sales price (ASP), question, 41
- Appendix slides, purpose, 262
- Applicant tracking system (ATS), 72, 146, 246
- Ashton, Josh, 202–203
- Ask for More (Carter), 74
- Attunement, 156
- Average sales price (ASP) information, quota, 48
- B
- Behavior, company values (impact), 132
- Beisel, Rachel, 10, 28–29, 254
- Belonging, building, 143
- Blake, Colleen, 123
- Blame, avoidance, 241–242
- Blanche, Aubrey, 16, 46, 135–137, 229
- Board of directors
- altitude, communication, 255
- appendix/pre‐read material slides, purpose, 262
- communication, 208–209, 255
- expectations, 110
- indicators perceptions, 248
- interaction process, 205
- interests, understanding, 210–211
- meeting, 210, 254
- members, connection/understanding, 208, 256–257
- metric, focus, 209
- overpromising, avoidance, 211
- presentations, 257–258, 263–265
- relationship, building, 103, 110, 257
- reporting, 56
- success, alignment, 89
- Board of director slides
- Brown, Analiese (promotion), 53–56
- Brown, Jennifer, 135, 185
- Bryant, Trier, 272
- Burnout, 229, 241–242
- Burnout (Nagoski/Nagoski), 229
- Business
- Bussgang, Jeffrey, 4, 22, 43–44, 49, 230, 232, 248–249
- Butler, Donna, 135, 137
- C
- Capital gains clock, 79
- Carter, Alexandra, 74–75
- Carter, Mary, 268–269, 271–272
- Cash, equity (contrast), 83–84
- Casnocha, Ben, 148
- Cass, Dave, 182–183
- Chapman, Diana, 134
- Chief Executive Officer (CEO)
- communication expectations, setup, 107
- interaction process, 205
- meeting, 70–71
- one‐on‐one agenda, sample, 105–106
- preferences, awareness, 207–208
- relationship, building, 103, 104
- responsibilities/work, 177–181
- role, difficulty (startup executive perception), 95–96
- success, 89, 94
- trust, building, 106–107
- values, alignment, 106–107
- vision, 70–71, 94–95
- work style, understanding, 206–207
- Chong, Allen, 128–129
- Churn, lagging indicator, 49, 214, 230, 246, 248–249
- Circle of control, understanding, 231–232
- C‐level team, partnership (building), 59
- Coaching, support, 275–276
- Co‐founder relationship
- Collaboration skills, 116
- Collaborative leader, improvisation (embracing), 123
- Colonna, Jerry, 127, 128
- Command and control leadership, avoidance, 182–183
- Communication
- Company
- Compassionate bosses, impact, 137–138
- Compassion, practice, 215–216
- Compensation
- Competition market, research, 42
- Complementary skills, hiring, 121
- Constructive feedback, usage, 108
- Consulting, usage, 36–37
- Content Delivery Network (CDN), 41
- Cost per acquisition (CAC), question, 41
- COVID
- Cross‐functional department head, failure (reaction), 228
- Cross‐functional partners
- Cross‐functional stakeholder buy‐in, 4
- Csikszentmihalyi, Mihaly, 115
- Culture
- Culture add, creation, 133
- Customer
- Customer lifetime value (LTV), increase, 150
- D
- D'Anzica, Emilia, 37
- Dashboards
- Data‐driven storytelling, mastery, 59–60
- Data, importance, 21
- Data Visualization for Business Professionals (Knafflic), 224
- Data visualization tools, 248
- Deal backwards/lead forwards perspectives, 250
- Demographics, importance, 19
- Department OKRs snapshot slide (reporting results), R/Y/G (usage), 260
- Department team, communication, 258
- Dethmer, Jim, 134
- Dilbert Principle, avoidance, 242
- Direct reports, one‐on‐one meetings, 167
- Dirt Road (startup life stage), 44
- Disruption, discouragement, 24
- Diverse and inclusive teams
- Diversity and inclusion (D&I)
- Diversity, equity, and inclusion (DEI) initiatives, 272
- Double arrow, 218
- Drucker, Peter, 14, 154
- Duffy, Mollie West, 176
- Dweck, Carol, 21, 58
- E
- Early‐stage startup
- Employees
- Engineering
- Entering Startupland (Bussgang), 43
- Equity, 75–76
- Execution‐focused duties, continuation, 53
- Executive coach, usage, 194
- Executives. See Startup executives
- big company executives, interaction, 109–110
- business skills, 192–193
- communication plan, creation, 241
- compensation, research, 75
- executive‐level leadership, transition (questions), 54–55
- executive‐level performance, results (connection), 54
- failure, reaction, 228–229
- first‐time executives, challenges, 31–32
- internal promotions, 66
- non‐executives, differences, 13–14
- promotion, 52–53
- responsibilities, 11
- seat offer, securing, 67
- specialization, usage, 56
- startup role, promotion process, 53–56
- Executives, role, 52–53
- Executive team, interests/hobbies/family (learning), 111
- F
- Failure
- Failure/improvement, willingness, 21
- Fair market value (FMV), 79
- Fame/blame cycle, 235
- Feedback, usage, 172–173, 222
- Feelings, embracing/boundaries, 176
- Feld, Brad, 256
- Fierce Self‐Compassion (Neff), 216
- Finance leadership, partnering, 60–61
- Financial literacy, application, 56
- Financial metrics, 250
- Financial shareholders, interaction (willingness), 21
- First‐time executives, challenges, 31–32
- Fishkin, Rand, 120, 251, 276
- Flatirons Tech (LGBTQ+ technology group), founding, 3
- Flow, 115
- Fosselien, Liz, 176
- Frei, Frances, 19, 133, 135, 158, 165
- Front Range, tech inclusion (increase), 3
- H
- Hamilton, Arlan, 135
- Happiness/fulfillment timeline, 125–126
- Harada, Matt, 36, 66, 76, 118, 176, 177, 182, 217–218
- Harts, Minda, 127, 135
- Hasson, Gill, 135, 137
- Heilbronner, Sue, 28, 161, 269
- Heinz, Matt, 92, 96
- Hendricks, Gay, 161
- High Growth Handbook (Gil), 116
- High Output Management (Grove), 193
- High‐performance team culture, building, 165
- High‐performing team, building/leading (startup executive responsibility), 15–16
- Highway (startup life stage), 44
- Hiring
- Hoffman, Reid, 148
- Holloway Guide to Equity Compensation, The, 76
- How to Be an Inclusive Leader (Brown), 135
- I
- Ideal customer profile (ICP), question, 41
- Improvisation, embracing, 123
- Inclusive leader, learning investment, 185
- Inclusive teams, creation, 134–135
- Individuality, respect, 138
- Information technology industry, global economic impact, 2
- Innocenzi, Sarah, 122–123
- Internal promotions, CEO perspective, 63–64
- Interviewing, 68–69, 73
- LGBTQ+ status, revealing, 71
- It's About Damn Time (Hamilton), 135
- L
- Lagging indicators, 246
- Lauck, Mindy, 30, 106–107, 208, 234
- Lawyer, hiring, 81–82
- Leaders
- Leadership
- command and control leadership, avoidance, 182–183
- executive‐level leadership, transition (questions), 54–55
- finance leadership, partnering, 60–61
- post‐COVID leadership, 197
- relationships, establishment, 34
- startup leadership, advancement opportunity, 234
- team, alignment decision/communication expectations, 45, 107
- transition, 28
- Leadership Development, industry value, 3–4
- Leading indicators, 246, 250
- Learning mindset (growth mindset), embracing, 58
- LinkedIn, usage, 42, 45
- M
- MacCaw, Alex, 35
- Making of a Manager, The (Zhuo), 193
- Management, 205
- Market, business performance (comparison), 256
- Marketing executive, accountability, 14
- Marketing OKRs, setting, 98–99
- Marketing qualified leads (MQLs), 246
- Market knowledge, learning, 193
- McKenna, Samantha, 29
- promotion, 31–32
- McLemore, Taylor, 223
- Meetings
- Mehta, Nick, 25, 63–64, 93, 208–209, 260
- Memo, The (Harts), 127, 135
- Mental Health and Well‐being in the Workplace (Hasson/Butler), 135, 137
- “Mentor Madness,” 273
- Mentors, 273–274
- Mentorship, 267–269
- Metrics, 12
- Mindset (Dweck), 58
- Mission, team comprehension, 150–151
- Mistakes, handling/navigation, 162, 163–164
- Mochary, Matt, 35
- Morriss, Anne, 19, 135, 165
- Motley, Chris, 94, 273–274, 276–277
- N
- Nagoski, Emily/Amelia, 229
- National Center for Women and Information Technology (NCWIT), 2, 3
- Neff, Kristen, 216
- Net Promoter Score (NPS), 45, 229
- question, 41
- Net Retention, question, 41
- Net revenue retention (NRR), 246, 247
- Networking, usage, 267
- No Hard Feelings (Fosselien/Duffy), 176
- No Meeting Day, usage, 163
- Non‐founder startup team member, promotion, 30
- Notice, giving (process/expectation), 238–239
- O
- Objectives and Key Results (OKRs), 246
- One‐on‐ones, creation/improvement, 167
- On target earnings (OTE), goal, 74
- “On the Bus or Off the Bus” conversation, 232–233
- Operating cadence, predictability (creation), 200
- Option pool plan, sample, 77–78
- Organization
- Outcomes/activity contrast, measures, 247
- Ownership, 176, 182
- P
- Parcells, 94–95
- Peacock, Chris, 11, 233
- Peer mentor, support, 274
- Peers, negative feedback strategies (navigation), 219–220
- Penner, Julie, 176
- Peper, Erik, 174–175
- Perel, Esther, 42–43, 139
- Performance, measurement (CEO interaction), 251–252
- Personal advisors, development, 270–271
- Personal life, professional life (wall), 35
- Personal retrospectives, usage, 123–126
- Pivots, navigation, 230–231, 233
- Pocrnick, Therese, 184–186
- Post‐COVID leadership, 197
- Power imbalance, abuse (avoidance), 17
- Pre‐read material, purpose, 262
- Presentation
- Problems, understanding, 153
- Project management skills, 116
- Promotions
- Psychological safety, cultivation/building, 137, 162, 183–184
- Public speaker, gravitas, 225
- R
- Radical Candor (Scott), 20, 104, 154, 172
- Rand, Erin, 33–35, 224, 238, 241–242
- Rand, Ray, 242
- Recruitment, 143
- Red‐yellow‐green check‐ins, 176
- Relationships, building, 103, 104, 110, 205, 257
- Remote work, usage, 199
- Reports
- Respect, usage/importance, 217–218
- Retrospectives
- Revenue Collective, compensation research, 75
- Revenue, lagging indicator, 248
- Rex, John, 11, 22–23
- Rice, Jennifer, 37
- Ruinous empathy, 152, 172
- S
- Safety protocols, 201–202
- Salary haircut, 47
- Scale‐up leadership mindset, early‐stage startup (contrast), 24–25
- Scaling, difficulty, 23
- Scaling startups, leaders (entry), 21–22
- Scorecards, usage, 248
- Scott, Kim, 20, 104, 152, 154, 172
- Secrets of Sand Hill Road (Kupor), 78
- Self‐compassion, practice, 216
- Senesi, Chris, 21
- Serviceable addressable market (SAM), question, 41
- Setbacks, 223, 226–227
- Shah, Hiten, 206–207, 230, 232, 235
- Shareholders, reporting, 56
- Short‐terms wins/long‐term priorities, balancing, 96
- Skip levels, problems, 173
- Smith, Nicole Wojno, 58–59, 210–211, 274
- Software, presentation, 69
- Sponsorship, support, 275
- Spreadsheets, usage, 248
- Stakeholders, work style (understanding), 108
- Start‐stop‐continue, 187–188
- Startup
- Startup Boards (Feld), 256
- Startup career
- Startup executives
- accomplishments, early focus, 93
- accountability, 13–14
- accountant, hiring, 80
- behavior, leading, 153
- boundaries, creation, 128–129
- burnout, 229
- cash/equity, contrast, 83–84
- CEO role perception, 95–96
- circle of control, understanding, 231–232
- commitment, 16
- communication/processes, feedback (usage), 172–173
- company leader, transition, 33–35
- compensation breakdown, 74–75
- context level, elevation, 18
- decisions, agreement, 233
- departmental understanding, 15
- development, 49
- differences, 9
- disagreements, 108
- early‐stage equity, 81
- empowerment, 5
- equity, 75–77, 79
- external/internal hiring, contrast, 64–65
- feedback, providing, 12
- functions, 11, 54
- goals, defining, 89
- growth, acceleration problem, 226
- high‐performing team, building/leading, 15–16
- hiring deal, negotiation problems, 84–85
- impact, 91–92, 218–220
- improvement areas, inventory list, 192–193
- involvement level, comfort, 47–48
- motivation, 55–56, 122
- non‐executive startup employees, companionship/camaraderie (reduction), 16–17
- notice, giving (process/expectation), 238–239
- offer, 73–75
- offer letter/contract (review), lawyer (hiring), 81–82
- operating cadence, predictability (creation), 200
- option pool plan, sample, 77–78
- outsourcing, 128
- performance measurement, CEO interaction, 251–252
- power imbalance, abuse (avoidance), 17
- priorities, change, 198–199
- privilege, understanding/impact, 126–127
- promotion, 53–56
- qualifications, 18–20
- quitting, decision, 223–224, 232, 236
- results, communication, 54, 252
- risk/reward, contrast, 75–76
- schedule, 12–13
- self‐knowledge, personal retrospectives (usage), 123–126
- selves/shadow sides, embracing, 127
- shortcomings, 120–121
- strengths, identification, 115–117
- tactical/strategic approach, balancing, 57
- talent delegation, learning, 24
- title, negotiation, 82
- underrepresented group, impact, 163–164
- value, proving, 90–91
- vesting schedule, understanding, 78
- Startup executives, role
- Startup fit
- Startup leaders
- Startup leadership, advancement opportunity, 234
- Storytelling With Data (Knafflic), 121
- Straight talk, 71
- Strengths, identification, 115–117
- Strengths, Weaknesses, Opportunities, and Threats (SWOT), 95
- Stress, reaction (differences), 217
- Stretch projects, 58
- Success, 94, 176, 182
- Support circle, usage, 159
- T
- Tactical skills, assessment, 192
- Talent
- Target market quota, 48
- Teams
- balance, creation, 135–136
- bench dream team, recruitment, 61
- bonuses/OKRs, connection, 151
- “Can We Talk” messages, avoidance, 170–171
- C‐level team, partnership (building), 59
- comfort, 160–161
- communication expectations, setup, 107
- company culture, defining, 131
- conflicts, 154, 173
- culture, 158, 165
- delivery, empowerment, 161
- department team, communication, 258
- diverse and inclusive teams, cultivation, 147
- empowerment, 63, 158–159
- executive team, interests/hobbies/family (learning), 111
- fun, 186
- health/wellness, understanding, 138
- hiring, 145
- inclusive teams, creation, 134–135
- inclusivity (support), work expectations (creation), 136
- inheriting, approach, 144–145
- interaction, agreements, 164
- members
- mission comprehension, 150–151
- mistakes, handling/safety, 162, 183–184
- OKRs, setting, 151
- “On the Bus or Off the Bus” conversation, 232–233
- pandemic leadership, 202–203
- performance cadence, creation, 166–167
- problem‐solving, teaching, 184
- problems, understanding, 153
- psychological safety, cultivation, 137, 183–184
- relationship, building, 103
- relaxation, usage, 174–175
- reporting, accountability (usage), 252
- research, 42
- resources, availability, 159–160
- rhythm, repair (practice/usage), 186
- roadmap, creation, 164
- schedules/time zones, handling, 200
- scorecard, creation, 146
- startup executive outsourcing, 128
- startup leader trust, building, 133–134
- structure, assessment, 92
- support, 138, 183
- supportive culture, creation, 133
- time off, ensuring, 174
- voices/wisdom, retrospectives (usage), 187
- Technology inclusion, increase, 3
- Tech Stress (Peper), 174–175
- Tedrick, Susanne, 2, 127, 135
- Therapy, usage, 171–172, 195
- Total addressable market (TAM), questions, 40, 41, 70
- Triangulation, 220, 235
- Trust, building, 106–107, 133–134, 158–159
- Twitter, usage, 45
- Tyson, Mike, 230
- Y
- Yeh, Chris, 148
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