Insurance… slow, outdated, and a frustrating experience for businesses. But it doesn’t have to be. For businesses and fast-moving startups / scale-ups, the customer experience has fallen far behind, leaving them underserved and at risk. At upcover, we’re flipping the script by providing innovative, tech-driven insurance solutions that businesses love—tailored, fast, and built for the pace of today’s world.

ABOUT UPCOVER

upcover is Australia's fastest growing business insurance platform for SMBs, startups and scale ups - trusted by 60,000+ small businesses across ANZ. We are game changing the decades old business insurance industry by creating digitally native insurance products in partnership with the world's largest insurers and underwriters. upcover's platform bridges the gap between cutting-edge technology and the complexities of insurance, ensuring our customers get the protection they need, simply and effectively.

WHY JOIN US?

The world of commercial insurance and underwriting is complex and analog. And its gigantic. Nearly $25B in business insurance is transacted across ANZ every year, and only 5% of this is online. upcover is at the forefront of digitising the industry and we are aided in our effort by the world's top insurers, underwriters and VCs.

We’re looking for a founding sales lead / AE who can both carry a quota like a killer IC and build the early system that future reps will run on.

• You’re hands-on, closing deals every week.
• You’re obsessed with systems, product, and data, not just charisma.
• You want to grow into Head of Sales as the company scales.

This is an IC role with high ownership and visibility across the business.

WHAT YOU'll OWN

• A personal new business and expansion quota in the SMB segment.
• The first real sales playbook (scripts, flows, ICP definition, pricing feedback).
• Early pipeline generation: some inbound, some outbound, some experiments.
• The foundations of hiring, onboarding, and enablement for the next 3–5 reps.

WHAT YOU'll DO (first 12 months)

Be our frontline seller

• Run the full cycle: prospect → qualify → demo → close → handoff.
• Take over most net new calls from the founders while keeping them close to key deals and insights.
• Maintain short, efficient sales cycles and constantly test how to make them faster:
• “Radically transparent” selling (clear strengths and weaknesses upfront).
• Tight ICP filtering so you reduce time-to-lose and don’t waste cycles.

Turn founder knowledge into a playbook

Sit with the founders and and our placement teams to pull the sales process out of their heads:

• What ideal customers look like.
• What pains resonate.
• What objection handling actually works.

Turn that into:

• A clear discovery framework (questions, depth, branching).
• A standard demo structure that reps can learn.
• Early email / call scripts and talk tracks, with room to iterate.

Start a simple “Hall of Fame” library:

• Save and annotate best call snippets that show great openings, discovery, and closes.

Design an early sales system

Define stages and conversion targets in the CRM.

Help choose, configure, and actually use:

• Call recording / analysis.
• Basic sales engagement tooling.

Start writing the first sales scorecard:

• DNA / mindset.
• Craft
• Specific knowledge

Partner with Product & Growth like a mini-CRO

Even as the first sales hire, you’re expected to think beyond your deals

Give structured feedback loops into product:

• Patterns you see across lost deals.
• Feature/config gaps that block adoption or cause churn.

Collaborate with Growth/Marketing (or the founder doing that job) to:

• Tighten our ICP and messaging.
• Decide where to invest next: inbound channels, lightweight outbound, partners, content.

Help instrument basic revenue analytics:

• Win rates by segment.
• Sales cycle length.
• ACV and early payback / LTV signals.

WHAT YOU BRING

Experience

• 2–5 years in B2B SaaS or tech-enabled SMB sales, with:
• Strong closing experience in short/medium sales cycles (days/weeks, not quarters).
• Exposure to SMB or mid-market where volume, speed, and process matter.

Skills & traits

• Hands-on closer. You like being on calls, handling objections, and asking for the sale.
• Systems brain. You naturally ask: “Why is win rate low?” and / or “Is this training, ICP, product, comp, or something else?”
• Product-curious. You want to understand how the product works and why it was built that way.
• Builder mentality. Happy to create the deck, write the first script, and tweak the CRM yourself.
• Good energy. Positive, resilient, and calm under pressure.

HOW WE MEASURE SUCCESS

In your first 12–18 months, success looks like:

• You’re consistently hitting or beating your personal quota.
• Basic pipeline and forecast visibility is in place
• We go from a founder-led motion to a clear, repeatable playbook that others can learn.
• We hire our next 5 reps against a clear scorecard you helped define.

OUR STACK (Indicative)

Hubspot, Lusha, Notion, Google Workspace, Slack

WHAT THE INTERVIEW PROCESS LOOKS LIKE

• Intro call with co‑founder (culture & role fit)
• Sales interview case
• Cross‑functional interviews (Ops/GTM/Product)
• References & offer

UPCOVER'S REMOTE FIRST SETUP

upcover is HQed in Sydney, Australia 🇦🇺 but has a team thats distributed across Australia 🇦🇺, India 🇮🇳, Spain 🇪🇸, Pakistan 🇵🇰, Italy 🇮🇹, Nigeria 🇳🇬, Iran 🇮🇷 , Sri Lanka 🇱🇰, Egypt 🇪🇬, Indonesia 🇮🇩, Philippines 🇵🇭 and Kazakstan 🇰🇿! And while fully remote, we are proud that everyone in our team operates with a very high level of autonomy and responsibility.

We index high on diversity and strongly believe that the best outcomes are the result of a culture that preserves individuality and independence while ensuring accountability. If you thrive in a self-directed, inclusive, and entrepreneurial setting, you’ll find our team to be the perfect place to grow and contribute. We have a very healthy pipeline of opportunities, and we’re moving into new territories by launching our own niche insurance brands with key insurance partners.

upcover is committed to employment equity and welcomes applications regardless of race, ethnicity, age, nationality, religion, disability, sexual orientation or philosophy of life.

Join us in redefining insurance!