Introduction
Despite being surrounded by co-founders, investors, board members, advisors, and teammates – all of whom are giving you a steady stream of input and advice – it can still feel like you’re on an island with no one to go to for some of your most pivotal decisions and problems. Working through executive compensation, an upcoming fundraise, a term sheet you just received, or a problem with your board are just a few examples of issues that fall squarely on the CEO. For these types of issues it’s often difficult to find a thought partner that truly understands all the angles and doesn’t have competing incentives.
Our engagement philosophy was born from this insight. While traditional executive coaching focuses entirely on building stronger leadership skills, managerial skills, and emotional resilience that are critical for success, they are only one side of the CEO coin. The tangible, tactical knowledge necessary to navigate challenges specific to the startup CEO are equally important. Said differently, learning the best stress-management techniques in the world won’t eliminate the stress coming from your current fundraising round, but successfully closing it will. Similarly, becoming a better leader and people manager will give you longer-term payback, but won’t help you come up with the optimal cash-equity split for this year’s executive bonus plan. Mastering the tactical components of your job – like creating the best possible fundraising deck, negotiating a term sheet, preparing for and running an effective board meeting, and structuring a sales compensation plan – will organically lower stress and improve your well-being, and materially increase the value of your company.
Below are our CEO Advisory modules. They combine insights from the very best thought leaders in the venture ecosystem with our experiences building companies from zero to scale, reaching a combined $100+ million in revenue, hiring over 500 employees, and raising over $300MM in total from leading venture capital firms. You will find actionable templates, readymade forms, and nuanced discussion on topics ranging from fundraising, to board management, and scaling your team. Each module stands on its own so go ahead and jump right to the section that targets your current most-pressing issue.
1.1. Fundraising
Fundraising is the lifeblood of your company and a necessary evil. It’s difficult to assess points of failure because of the numerous interdependencies, and it’s even more difficult to master. We’ve distilled down the best templates, guidelines, and rules to follow in your fundraise from our experiences raising over $300MM for our own companies and we’ve also incorporated the best ideas from the most prolific fundraisers of our time.
1.2. Talent Acquisition and Management
One of the most important things that you will do as a CEO is setting the culture and building your team. They will ultimately be limiters on your success. And your team compensation and benefits will almost definitely be the largest expense on your income statement. From hiring hundreds of employees ourselves, we have distilled down our most valuable lessons-learned.
1.3. Board of Directors and Investor Management
Mastering board management is crucial, yet it's perhaps the least intuitive aspect of CEO duties. You might feel that its a distraction, or feel tempted to present only the good news (like you might in your investor deck) — common misconceptions that we’ve been guilty of ourselves. But here's the reality: adept board management is vital for success. Below, find our detailed playbook, complete with agendas, board deck templates, sample investor update emails, do’s and don’ts, and more to turn this complex task into a powerful asset for your company.
1.4. Sales and Go-to-Market
One of our main jobs as CEO is to sell. You sell investors on investing in you. You sell candidates on joining your company. You sell your employees on your vision. You also have to sell your customers. Understanding how to build out a sales org to support you and ultimately knowing when to hire yourself out of a direct sales function is a delicate balance. We have compiled some of the best ideas from the most respected sales leaders combined with our own experiences of building out large sales teams from scratch to help you navigate this important function.
1.5. Strategy and Finance
Strategy and Finance: the backbone of your startup's success. Navigating the intricate balance between finding product-market fit, weighing growth against profitability, and managing your runway and cash reserves are all make-or-break responsibilities that you own. These are not just operational tasks; they're the lifeblood of your venture's future. In the following section, we delve into each of these critical areas with frameworks to help you simplify them and manage them with more clarity.
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