Fractional Head of Sales / SaaS Sales Advisor – Part-Time Contract

We are looking for an experienced B2B SaaS sales leader to help us assess, refine and formalise our sales approach.

The immediate objective is not to recruit and manage a large sales team. It is to work alongside the founder to identify what is working, resolve gaps in our go-to-market approach and establish the foundations for a repeatable sales process.

By the end of the initial engagement, we expect the advisor to have:

• Assessed our existing customers, pipeline, sales activity and conversion data

• Helped sharpen our ideal customer profile and priority market segments

• Reviewed our positioning, sales messaging and value proposition

• Defined clear pipeline stages, qualification criteria and sales metrics

• Reviewed selected sales calls and provided practical coaching

• Recommended improvements to our CRM and sales operating rhythm

• Created a prioritised 90-day sales action plan

• Advised us on when and whom to hire as our next sales resource

If there is a strong mutual fit, the engagement may develop into an ongoing Fractional Head of Sales position.

The Opportunity

Taskr is an early-stage SaaS business helping multi-site operators to close the gap between strategy and execution.

We have achieved modest sales to date in our brief time in operation, and are now ready to make our approach to sales more focused, measurable and repeatable.

Until now, sales have primarily been founder-led. We are looking for an experienced B2B SaaS sales operator who can work alongside our founder in an advisory and hands-on capacity.

This is an opportunity to influence our commercial direction at an important stage of the business without initially committing to a full-time role.

During the initial 6–8 week engagement, you will help us:

• Review our existing customers, pipeline and sales performance

• Clarify our ideal customer profile and priority market segments

• Strengthen our sales messaging and value proposition

• Review our pricing and packaging from a sales perspective

• Develop a practical and repeatable sales process

• Define qualification criteria, pipeline stages and core sales metrics

• Improve CRM discipline, forecasting and follow-up

• Review sales conversations and coach the founder

• Identify the most important sales experiments for the next 90 days

• Determine the appropriate timing and profile for our next sales hire

You’ll provide strategic guidance, but you must also be comfortable working directly with real opportunities, calls, data and sales materials.

You are an experienced SaaS sales leader who has personally helped an early-stage B2B software business progress from founder-led selling to a more predictable sales model.

Ideally, you can demonstrate:

• Experience as a Head of Sales, VP Sales, CRO, Fractional Sales Leader or SaaS founder

• A track record of building or materially improving an early-stage B2B SaaS sales function

• Experience selling to [SMBs / mid-market businesses / enterprise customers]

• Experience with contract values and sales cycles similar to ours

• Strong capability across ICP definition, qualification, messaging, pipeline management and sales execution

• The ability to distinguish between a sales execution problem, a positioning problem and a product-market-fit problem

• A practical, evidence-based approach rather than reliance on a generic sales methodology

• Strong coaching and communication skills

• Comfort working directly with founders in a fast-moving, resource-conscious environment

• The ability to provide specific examples and measurable results from comparable businesses

Australian market experience is [essential/preferred], particularly if you also understand how Australian SaaS businesses can sell into [North America/APAC/global markets].

This is initially a paid advisory engagement with hands-on involvement.

We are not looking for:

• A generic business coach

• A lead-generation agency

• Someone whose primary recommendation will be to immediately hire a large sales team

• An executive whose experience has only been within mature, well-resourced organisations

• A consultant delivering a strategy document without helping us apply it

We want someone who can diagnose our current position honestly, focus us on the right priorities and help us build the foundations for sustainable growth.

• Initial engagement of 6–8 weeks

• Approximately 4–8 hours per week

• Hybrid working arrangement

• Paid on an hourly basis

• Potential to continue as an ongoing Fractional Head of Sales

• Expected commencement: 15 August, 2026

• Remuneration: $70-$110/hr commensurate to experience

Please submit your CV or LinkedIn profile together with a short response covering:

1. The early-stage SaaS business in your background most comparable to ours.

2. Its approximate starting stage, target customer, contract value and sales model.

3. What you personally changed or implemented.

4. The measurable commercial result.

5. What you would want to understand during your first two weeks with us.

6. Your availability and expected hourly, daily or project rate.

Shortlisted applicants will be invited to an initial discussion with the founder.

We welcome applicants from different backgrounds and are primarily interested in relevant experience, demonstrated results and fit with the current needs of the business.