CEO Search

Interim CEO

Qualities we’re looking for in CEO candidates (interim and permanent):

1. Track Record: Y Combinator Alumni is a must. Strong financial, analytical, strategic and problem solving skills.

2. Leadership Ability: Is this person inspiring? Empathetic? Have adaptable leadership skills? Would I join their company?

3. Founder Charisma: Would this person be successful at leading the Seed round? High emotional intelligence and the ability to win hearts and minds. Has an attitude of “Think big, then think bigger”

4. Industry / Domain Experience: Does this person have passion for open source software and for building enduring businesses. Do they have a vision for the project’s impact on the market?

5. Drive / Ambition: Strong career trajectory. Joining OCV company for the right reasons.

6. Speed/Iteration: Can this person thrive in a rapidly changing environment? Do they drive change or simply let it happen?

CEO interview process

1. Initial conversation with Recruiting: In this initial conversation, we want to know more about the CEO candidate as a person and their interest in this role. The candidate should be prepared to discuss logistics such as location, and availability to start a new role and learn about the OCV model.

2. Interview with the OCV COO: In this second conversation, we evaluate the candidate’s skills, experience, and work history. The interviewer will also discuss more details concerning the project and the team.

3. Interview with Consulting or General Partner: In this round, the candidate meets with OCV General Partner to discuss the vision for the project and company.

4. Meet the Company CTO: This will be several conversations to determine the fit in developing a partnership. Complete and discuss this questionnaire together.

5. Meet the Company existing team: In the final round, the CEO candidate meets with additional team members as appropriate.

6. Reference checks: We request that candidates provide four references before making an offer. See additional details on reference checks at General interview process .

Tips to OCV CTOs to find the ideal co-founder for their business

1. Look for someone with complementary skills: When selecting a co-founder, it is important to look for someone whose skills complement your own.

2. Look for someone who shares your vision: Your co-founder should share your vision for the company and challenges you to make it better. This will help ensure that you are both working towards the same goals and that you are both passionate about the business.

3. Look for someone you trust: Your co-founder will be your partner in the business, so it is important to choose someone you trust. Look for someone who is reliable, honest, and has a good track record.

4. Look for someone who is committed: Starting a business is hard work, so it is important to choose a co-founder who is committed to the business. Look for someone who is willing to work hard, put in the time and effort, and is willing to make sacrifices to help the business succeed.

5. Look for someone you get along with: Building a business can be stressful, so it is important to choose a co-founder who you get along with. Look for someone who shares your values, your work ethic, and appreciates your sense of humor.

Questions to ask your potential co-founder

General alignment

1. Why do you want to join us as CEO? What are you personal goals in this endeavor, both financial and non-financial?

2. Walk through their resume; why did they leave and join each organization? - search for motivation and honesty

3. What would you have done differently at each org in your past if you were the CEO? - search for strategic insight

4. What would you change with our product today? - have they done their homework, can tell what’s currently wrong

5. What are your strengths and weaknesses and where do you want to spend most of your time? How would that change as the company matures?

6. How many hours are you willing to work in a week would you be willing to take calls at odd hours and what are the boundaries that we should respect?

7. What would be an ideal exit for you: IPO or acquisition? If acquisition, what price would we consider a win?
1. In what time frame? 2 years? 5 years? 10+ years?

8. What culture would you like to build at our company?

9. Rank these in terms of importance: making money, building a product, or building a team?

10. Who would your ideal investors be and how much money do you want to raise?

11. How would we divide responsibilities? Resolve conflicts between ourselves?

12. What are your thoughts around pivots? Are you only interested in the current vision of the business?

13. What is your mantra around speed, iteration, in balance with quality?

14. For OPCs (OCV Public Benefit Companies) - What is your perspective on the impact of this on our business? How can we deliver on this public benefit?

Product and market

1. What were some of your sales experience / learnings in building prior startups?

2. Are you going after building a new category or a better product in an existing category?

3. What are the large players already if this is an existing category?

4. Where will the budget come from if this is a new category?

5. How do you think we should position ourselves relative to other players in the industry?

6. Does your solution have enough value to justify a customer pay additional money or move or move the budget to your solution? What is our value proposition and competitive advantage?

7. How should we refine our approach to existing and potential customers to better meet their needs?

8. What's the long-term view of this market - will this combine with another category or will you believe this will become a standalone? How might the industry otherwise change in the next five to ten years?

9. Why does it matter to have the open source community and business be in alignment? How might we better engage the community to show good stewardship?

10. Of the company’s existing or planned features, how optimized do you think their placement is in our priced and not priced offerings?

11. Of the open issues in the open source software project, is there anything you’d identify as high priority to work on in order to commercialize successfully? Are there any new issues you’d raise as essential to resolve?

Help us sell your opportunity to a potential CEO

1. Provide a short bio and background on you the founder

2. What are you excited about (your company) project? What is your north star goal for the impact (your company) will have on the community and users of the product?

3. What aspects of being a founder have you loved?

4. What aspects of being a founder would you love to have the CEO take over?

5. What skills or personality traits do you think a new CEO should have to complement what you bring to the table?

Additional references: