About Cliffside Cybersecurity

Cliffside is a Sydney-based cybersecurity advisory and services firm, founded in 2014, working with mid-market and enterprise Australian organisations in energy, financial services, government and critical infrastructure. We tell clients what they actually need, not what we want to sell. We assess first, then recommend. We regularly talk clients out of spend they do not need, which costs us revenue in the short term and earns us relationships that run for years.

Our work spans security strategy and architecture, compliance and audits (ISO 27001, Essential Eight, APRA CPS 234), cloud security, penetration testing and managed services including SOC monitoring. Engagements are led by senior practitioners, not presenters. We hold an ISO/IEC 27001:2022 certified ISMS and have been lead auditors since 2008.

Our buyers are CIOs, CISOs, CTOs and security managers carrying real regulatory and operational pressure.

The role The Sales Development Representative opens the conversations our consultants close. This is a full-time hybrid role based in Sydney, with genuine flexibility to work from home, and part time arrangements considered for the right person.

Day to day, you will:

- Identify and qualify mid to large Australian organisations in energy, finance, infrastructure and education
- Run outreach by phone, email and LinkedIn, then nurture the leads worth nurturing and drop the ones that are not
- Book discovery meetings for senior consultants and keep the CRM accurate enough that others can rely on it
- Work alongside consultants to understand the services properly and build messaging that reflects what we actually do
- Track what is moving in the market, feed it back, and improve the process rather than repeat it

The role is measured, and we would rather you knew that now than in month two.



You will carry weekly activity targets and a monthly target for qualified discovery meetings that turn into real opportunities, with commission tied to the work that closes.

We will be straight with you about the numbers before you accept the role, and we expect you to be straight with us about whether they are achievable with the territory in front of you.

We are also not hiring a script reader. If a prospect does not need what we sell, say so and move on.

You will never be asked to manufacture urgency or push a service to hit a number. The pipeline you build has to survive a discovery call with a sceptical CISO, so it needs to be real on the way in.

What you need

Experience helps, but how you deal with people matters more. We would rather train product knowledge than fix a habit of overselling.

- Prospecting and qualification experience in B2B, including the judgement to be honest about which parts of a pipeline are real
- Comfort working to activity and pipeline targets, and the honesty to flag early when a number is not going to land rather than manage it quietly
- Confidence on the phone and in writing with both technical and non-technical stakeholders: discovery calls, objections, rapport
- Business development instincts: spotting a target segment, supporting a campaign, and working with consultants on outreach that fits the audience
- Working knowledge of CRM and sales enablement tools, plus the discipline to record activity and outcomes accurately
- A real interest in cybersecurity, technology services or B2B professional services in regulated industries. You do not need to be technical on day one, but you do need to be curious enough to learn quickly
- The self-management to perform in a hybrid setup without someone watching
- Study in business, marketing or communications is useful, and prior SDR experience in tech or B2B is well regarded. Neither replaces being straightforward with people

📌 Sales Development Representative (Sydney)
🏢 Cliffside Cybersecurity
📍 Sydney