About Open Insurance

We are a venture-backed technology company disrupting a multi-trillion-dollar industry that has remained largely unchanged for decades. Our platform uses modern infrastructure and AI to bring greater transparency, efficiency, and better decision-making to a highly fragmented market.

We closed the largest pre-seed in insurtech history, backed by Tier 1 VCs and the largest strategics in the space. We have strong early market traction, a differentiated product, and a founding team with a proven track record of building and scaling category-defining companies. We're growing quickly and investing in the people, systems, and technology that will support the next stage of growth.

Why This Role

We are hiring a Chief of Staff to support Open Insurance’s sales team as we scale our go-to-market motion.

Reporting to the Head of Growth, you’ll help streamline operations, keep meetings and demos running flawlessly, manage communication workflows, and maintain structure across the sales pipeline. Your work will directly free up senior sales leaders to focus on strategy and relationship-building while follow-up, organization, and execution are handled with excellence.

You’ll support demo preparation, prospect research, calendar and CRM management, and sales reporting, all with the accuracy and discretion senior leaders need to trust you with their calendars and their pipeline. If you’re highly organized, thrive behind the scenes, and want real ownership over how a sales team runs, you’ll have significant visibility and responsibility from day one.

What You’ll Own

- Inbox and calendar management:



organize and manage scheduling across multiple sales leaders’ inboxes and calendars each week.
- Sales calendar ownership: maintain the sales calendar for key milestones, including QBRs, expansion meetings, and property engagements.
- CRM and pipeline hygiene: maintain HubSpot deal hygiene, log follow-ups from meeting notes, and keep deal stages current.
- Pipeline reporting: prepare weekly pipeline reports and monthly summaries covering conversion, expansion, and new logo metrics.
- Demo and meeting preparation: research prospects and target properties, and prepare customized presentation decks ahead of every sales call.
- Prospect research: gather intelligence on target companies and decision-makers to support tailored, well-informed sales conversations.
- Contract and onboarding coordination: prepare and track partner contracts, and manage the onboarding calendar and internal handoffs.
- Sales enablement and content: maintain sales collateral, FAQs, and templates, and support LinkedIn content planning and event follow-up.

What We're Looking For

We are looking for a highly organized, discreet, and dependable Executive Assistant who thrives operating behind the scenes of a fast-moving sales team.





- 3-5+ years of experience as an Chief of Staff/Executive Assistant, Sales Coordinator, or similar support role.
- Exceptional organizational and written and verbal communication skills.
- Strong research and presentation skills, with experience in PowerPoint, Google Slides, or Canva.
- Proficiency with CRM tools, HubSpot strongly preferred.
- Highly detail-oriented with excellent time management and follow-through.
- Comfortable working independently and juggling multiple priorities without close oversight.
- Tech-savvy and adaptable to fast-changing tools and systems.
- High integrity, discretion, and professionalism handling sensitive information.

How We Work & Who We Are

- Remote-first by design: you’ll operate independently across time zones, with the structure and communication habits that keep a sales team moving without needing to be in one room.
- Low process, high context, flat by design. We organize around the belief that category-defining companies are built by people with chips on their shoulders and a hunger to own outcomes of increasing scope.
- Autonomy by default. The best cultures are built on intrinsic motivation, not management. We hire people we do not have to manage and give them room to operate.
- Best idea wins. We want people who generate sharp ideas, defend them well, and update fast when evidence moves. We are obsessed with ground truth.

Compensation

- Competitive base salary, based on experience.
- Comprehensive technology package with remote-first flexibility.

📌 Chief of Staff (Sales) (Colombia)
🏢 Open Insurance
📍 Colombia