Insurance… slow, outdated, and a frustrating experience for businesses.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 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