Enterprise Sales Executive

Enterprise Sales Executive - New Business (Insurance / B2B)

Caava Group | Nairobi, Kenya | Founder-assisted enterprise sales role

This is a demanding, field-heavy role for a disciplined new-business builder. The mandate is to create pipeline, shape real opportunities, and keep complex enterprise deals moving so founders and senior executives can enter at the right moments to help close.

Reports to

Chief Growth & Innovation Officer

Primary focus

Caava Evolve, Caava AI, TurnQuest V4 upgrades and AMC uplift

Working model

High-accountability commercial engine role within a founder-assisted close model

Travel

Client-facing, with local and regional travel as needed

About Caava Group

Caava Group is building practical, trusted insurance technology for African insurers and distribution partners. Our work spans core modernization, AI-driven workflow outcomes, distribution enablement, and structured upgrade paths for mission-critical environments.

What this role is really about

• Building and running the new-business engine across named target accounts and selected strategic opportunities.

• Originating and qualifying opportunities early enough that the business is no longer dependent on walk-ins or founder discovery.

• Preparing opportunities properly: stakeholder maps, value hypothesis, next steps, proposal coordination, procurement path, and close-readiness.

• Using founder and senior executive time well by bringing them into deals when trust, solution shaping, or executive reassurance is required.

• Maintaining a clean commercial operating rhythm: no ghost deals, no vague updates, and no serious opportunity going stale.

What you will do

• Build and manage a focused target-account list across priority insurers, bancassurance institutions, and strategic partners.

• Run structured outreach using referrals, executive introductions, direct prospecting, events, and warm relationship paths.

• Lead discovery and shape opportunities around real business pain, urgency, and value.

• Map business, technology, operations, procurement, and executive stakeholders in each active opportunity.

• Coordinate proposals, solution notes, pricing inputs, and SOW support with product, delivery, finance, and leadership teams.

• Track procurement, security, legal, and approval steps so priority deals continue to move.

• Maintain high-quality pipeline reporting, next-step discipline, and weekly commercial hygiene.

• Support clean handover into delivery once work is signed.

Who this role suits

Strong fit

Organized, persistent, self-starting enterprise sales builders who enjoy creating momentum, structure, and commercial clarity.

Mindset

Comfortable working in a lean, founder-led environment where preparation, follow-through, and judgment matter more than title.

Commercial style

Able to prospect proactively, multi-thread accounts, write clearly, and keep complex opportunities moving without constant prompting.

Client posture

Comfortable in mission-critical sales contexts where trust is earned through credibility, detail, and disciplined follow-up.

You may not be a fit if

• You mainly manage existing accounts rather than create new pipeline.

• You rely heavily on inbound leads or broad marketing support.

• You want a senior commercial title more than a demanding execution role.

• You dislike detail, written follow-through, meeting preparation, or pipeline discipline.

• You expect to operate as a lone closer without collaboration with founders, product leaders, and delivery teams.

Preferred background

• 4-7 years in B2B sales, enterprise sales, business development, or commercial account growth.

• Experience in insurance, insurtech, fintech, enterprise software, IT services, or another complex-solution environment.

• Comfort engaging business, operations, technology, procurement, and executive stakeholders.

• Strong written and verbal communication, including proposal support, briefing notes, and client follow-up.

• Evidence that you have personally helped create and advance meaningful commercial opportunities.

Compensation and growth

Competitive fixed salary with meaningful performance upside, aligned to a founder-assisted enterprise sales model. The role is designed for someone who can grow into broader commercial responsibility over time.

How to apply

• Submit your CV.

• Include a short note on why this role fits you.

• Provide three examples of opportunities or deals you personally helped create and progress, including: what was being sold, your exact role, how the opportunity originated, who the key stakeholders were, and what happened in the end.

Applications that do not show concrete commercial ownership, opportunity progression, and disciplined follow-through will not be prioritised.