Regional Sales Manager - Mid Market

We're looking for a

Regional Sales Manager - Mid Market

This role is Remote, Australia

This is a pure net-new business role: the mandate is to bring in new logos within an assigned geographic territory, building strong market coverage and creating demand across a diverse portfolio of prospective customers.

Success is measured on new bookings — pipeline generated, opportunities created and deals closed with organisations that are not currently Cornerstone customers. Success also means truly owning your patch: knowing the priority accounts, understanding where the opportunities are, building relationships across your market and creating enough activity and pipeline to consistently deliver your number.

The sales motion combines consultative, outcome-led selling with the pace, discipline and repeatability required in Mid-Market. You will work closely with BDRs, Solutions Consulting, Marketing, Partners and other specialists, while taking personal ownership for creating and progressing opportunities across your territory.

We believe in proof prior to product. The goal isn't to lead with a feature list or immediately jump to a demo. It is to understand what's changing for the customer, identify the resulting business and workforce problem, establish why it matters now, and connect Cornerstone to an outcome worth solving.

In this role you will...

Consultative Discovery & Customer Engagement

• Gain a strong understanding of a prospect's business priorities, workforce challenges, technology environment and desired outcomes before proposing a solution.
• Lead conversations that move from what is changing → business problem → workforce problem → why now → who cares → required outcome.
• Translate customer challenges into clear, relevant workforce use cases that connect technology to measurable business outcomes.
• Lead with the customer's problem rather than starting with Cornerstone's products.
• Adapt your discovery and messaging across different industries and customer environments within your geographic territory.
• Ask questions that go beyond traditional HR technology — exploring how work, roles, skills and capability are changing and what that means for the organisation.
• Recognise patterns across your territory and use those learnings to make future customer conversations faster, sharper and more relevant.
• Partner with Solutions Consulting when deeper technical discovery, solution design or demonstration is required.
• Bring a builder mindset to the sales process — curious, commercially creative and willing to test new approaches.
• Keep the sales process simple where possible: understand what the customer actually needs, bring in the right resources at the right time and maintain momentum.

Mid-Market Territory Development & Prospecting

• Own an assigned mid-market territory and develop a clear plan for how you will penetrate, prioritise and grow that market.
• Identify and prioritise target accounts based on opportunity, propensity to buy, business triggers and whitespace.
• Build and maintain a healthy pipeline of net-new logos through consistent self-generated prospecting, BDR collaboration, Marketing activity, partner referrals and local market relationships.
• Create broad coverage across your territory rather than relying on a small number of large opportunities.
• Maintain pipeline coverage appropriate to your conversion rate and proactively create pipeline before it becomes a quarter-end problem.
• Develop strong knowledge of the organisations and business community within your geography and identify relevant market triggers that can create customer conversations.
• Use repeatable campaigns, customer stories, events and workforce use cases to create demand efficiently across multiple accounts.
• Develop and evangelise workforce use cases across skills intelligence, workforce planning, learning, talent and AI.
• Position strategic entry points into broader customer conversations, while identifying natural pull-through opportunities across the wider Cornerstone portfolio.
• Work closely with BDRs to create coordinated account activity and maintain a consistent prospecting rhythm.
• Leverage Marketing and Partners to extend your reach across the territory and create additional routes into target accounts.
• Continuously test, learn and adapt — understanding which messages, personas, use cases and activities are creating conversations and doubling down on what works.

Full-Cycle Sales Execution

• Own the complete sales cycle end-to-end: territory planning, prospecting, discovery, solution positioning, demonstration, business case, proposal, negotiation and close.
• Balance velocity with quality — progressing opportunities efficiently without sacrificing good discovery.
• Lead with the customer's problem and desired outcome rather than the product — sell the problem before selling the solution.
• Translate Cornerstone's capabilities, including AI and workforce intelligence, into clear and measurable business value.
• Sell intelligence and outcomes, not just software — connecting workforce data, insights and AI capabilities to decisions customers need to make.
• Build concise, compelling use cases and business cases appropriate to Mid-Market customers.
• Build relationships across multiple stakeholders, from HR, Talent and L&D leaders through to IT, Finance, Transformation, Operations and executive sponsors where appropriate.
• Understand the buying process early and create a clear mutual path to decision.
• Create urgency by establishing a credible why now, rather than relying on artificial sales timelines.
• Take a consultative approach to diagnosing workforce and talent challenges and proposing the right combination of technology, services and partner capability.
• Protect and complement customers' existing HR technology investments by showing how Cornerstone can help those investments work better.
• Be confident creating demand around emerging use cases where the customer may not yet have a defined project, buying category or budget.
• Know when an opportunity needs deeper technical or executive support — and when it doesn't.
• Maintain momentum throughout the sales cycle and proactively remove blockers to decision.
• Consistently meet or exceed new-business quota, pipeline creation and revenue targets.
• Forecast accurately and maintain high-quality opportunity and pipeline data.

Deal Support & Handoff

• Partner with Solutions Consulting and technical resources at the appropriate stages of the sales cycle.
• Bring the right Cornerstone resources into opportunities without unnecessarily over-engineering the sales process.
• Collaborate with Marketing, BDRs, Partners, Legal, Deal Desk, Services and Customer Success to progress and close opportunities.
• Identify when a partner-led approach can provide greater reach, capability or commercial value to the customer.
• Ensure customer requirements, use cases, expected outcomes and commitments are clearly captured before handoff.
• Collaborate with Legal and Deal Desk to structure and finalise new-customer agreements efficiently.
• Own a clean transition into Implementation and Customer Success so the customer experience reflects what was agreed during the sales cycle.
• Capture and share learnings from wins and losses so the broader team can improve messaging, campaigns and execution across other territories.

You’ve got what it takes if you have...

• Strong technology, SaaS, data, AI or transformation-oriented sales experience, ideally working with Mid-Market or lower-enterprise customers. You don't need to come from traditional HR technology — we're interested in sellers who understand how technology can solve real business problems.
• A track record of consistent quota achievement and net-new logo acquisition.
• A genuine hunter mentality — you're comfortable creating your own opportunities rather than waiting for pipeline to arrive.
• Experience owning a geographic territory and the discipline to prioritise where you spend your time across a large number of potential accounts.
• Strong prospecting skills and comfort using multiple channels to create conversations with customers who don't already know you.
• The ability to manage a higher-volume sales motion while still delivering strong discovery and consultative selling.
• Strong territory, pipeline and time-management discipline.
• Commercial curiosity about AI, data and emerging technology. You don't need to be an AI engineer, but you should genuinely want to understand how AI is changing work, roles, skills and workforce decisions — and be excited about taking those conversations to customers.
• The ability to sell intelligence and outcomes, not just software — connecting data, workforce insights and AI capabilities to decisions a customer needs to make.
• The curiosity to ask questions beyond traditional HR technology: What work is changing? What capabilities will you need? What skills do you already have? What could AI augment or automate? Where are the gaps?
• The ability to move comfortably between HR conversations and broader business conversations with IT, Transformation, Operations and executive stakeholders.
• Strong business acumen and the ability to connect workforce challenges to strategic priorities and measurable value.
• A "figure it out together" mindset — comfortable operating where the answer isn't always obvious and willing to collaborate to find it.
• Confidence selling emerging propositions and creating demand where a customer may not yet have a defined project, buying category or budget.
• An understanding of SaaS commercial models and technology buying processes, even if your background isn't exclusively SaaS.
• Confidence using AI and modern sales technology yourself — to research accounts, identify signals, personalise outreach and improve your productivity.
• The ability to articulate complex ideas simply, particularly when selling new concepts such as workforce intelligence, skills intelligence and AI.
• The judgement to know when to bring in Solutions Consulting, Partners or leadership and when to keep an opportunity moving yourself.
• Strong communication, presentation, negotiation and creative problem-solving skills.
• The ability to operate autonomously while actively contributing to the broader team.
• A strong learning mindset: curious about your customers, territory and technology, and willing to continually test, learn and adapt.
• Low ego and high accountability. You own your territory, your number, your pipeline, your commitments and your development — while recognising that the best outcomes come from working as a team.
• A "no brilliant jerks" mindset. We want high performers, but how you win matters. You collaborate, share what you learn, help your teammates succeed and make the people around you better. Individual brilliance is great; brilliance at the expense of the team isn't.
• Willingness to travel within your territory as required for prospect meetings, events, discovery and closing activity.

At Cornerstone, we want people who are ambitious about what they can achieve individually and what we can achieve together.

We're building a high-performance sales culture where curiosity, accountability, collaboration, pace and a willingness to challenge the status quo matter just as much as the number.

We don't expect you to know everything on day one. We do expect you to be curious — about your customers, about AI, about data, about how work is changing and about what's possible when technology and workforce intelligence come together.

Our Culture:

Spark Greatness. Shatter Boundaries. Share Success. Are you ready? Because here, right now – is where the future of work is happening. Where curious disruptors and change innovators like you are helping communities and customers enable everyone – anywhere – to learn, grow and advance. To be better tomorrow than they are today.

Who We Are:

At Cornerstone, we believe in AI that works in the service of people, amplifying their judgment to drive high-performing, future-ready organizations forward. Cornerstone Workforce AI™, the intelligence platform for workforce readiness, brings together workforce and labor market data into a proprietary Cornerstone People Graph™, translating signals into intelligence, targeting learning where it matters, developing critical skills, and surfacing hidden talent. Delivered as an open, enterprise platform across whatever application your people work in every day, Cornerstone Workforce AI is built for scale, security, and trust, with certified AI guardrails. As an industry leader, Cornerstone is helping approximately 7,000 organizations, 140M+ users, across 186 countries build continuous workforce readiness.

Total Rewards:

At Cornerstone, we are dedicated to inspiring excellence and pushing boundaries in everything we do. Our compensation strategy is based on three fundamental principles: equitable pay, market-driven research, and skill-based appraisals. As part of our mission to share success and empower individuals to thrive in an ever-changing world, the listed salary range is just one element of Cornerstone’s comprehensive compensation package. This compensation package may also include annual bonuses, short- and program-specific awards depending on the role, and a comprehensive benefit offering. The disclosed salary range reflects the geographic differential based on the location of the position if applicable. The starting salary for the successful applicant will depend on several job-related factors, including education, training, experience, certifications, location, business needs, and market demands. This range is based on a full-time position and may be adjusted in the future. Join us in shaping the future of work — tomorrow, together. Experience flexibility and empowerment in your career at Cornerstone.

Check us out on LinkedIn, Comparably, Glassdoor, and Facebook!