Head of Sales / GM

Fifth Dimension AI; Singapore; Hybrid; SGD 193,000 - 258,000; Full time

Job summary

A leading technology firm is searching for a Head of Sales / GM based in Singapore. This pivotal role involves driving revenue growth across the Asia-Pacific region and establishing the commercial strategy. We seek an ambitious sales leader with a proven track record in closing significant deals and building effective sales foundations. The ideal candidate should possess deep AI/SaaS expertise and experience navigating diverse market landscapes. Competitive salary, equity, and generous benefits are offered, with a focus on hybrid work schedules.

Benefits

Highly competitive salary and OTE

Meaningful equity

Company-sponsored medical, dental, and life insurance

Unlimited Annual Leave

$1000 annual training budget

$100 monthly well-being budget

Tailored support for exceptional challenges

Qualifications

• Proven sales experience at early-stage to growth-stage B2B SaaS companies.
• Enterprise sales expertise with a track record of closing six and seven-figure deals.
• Experience establishing sales operations in new geographic markets.
• Ability to combine strategic thinking with hands-on execution.
• Must be a Singapore Citizen, Permanent Resident, or hold a valid work pass.

Responsibilities

• Own and exceed aggressive revenue targets for the APAC market.
• Develop and execute enterprise sales strategy focused on major deals.
• Establish Fifth Dimension as the category leader in AI real estate technology.
• Design and implement sales methodologies tailored for APAC.

Skills

Sales leadership

Enterprise sales expertise

Market development

Strategic thinking

Cultural agility

Technical product expertise

Education

B2B SaaS experience

Sales operations establishment

Tools

CRM and sales automation expertise (HubSpot)

Job description

About Us:

Fifth Dimension is building the all-in-one platform for commercial real estate, vastly outperforming horizontal AI players on complex tasks requiring deep enterprise and institutional knowledge. We have an established international customer base of Enterprise CRE companies, strong traction across U.S. and Europe as well as some customers in APAC 🚀

We’re a hypergrowth early‑stage startup with ample runway, backed by Tier 1 European and American investors - in the last year we’ve seen 7x ARR growth and 13x product usage. We currently have offices in London and New York, and a Singapore office opening in Q1 2026 - of which you’ll be a founding member. 🇸🇬

The founders, Johnny Morris and Dr. Kate Jarvis, are both data nerds 💻 But that’s not all! Johnny's got 16 years’ experience applying data and analytics to Real Estate, our GTM niche, and Kate's got a PhD in Linguistics from Stanford and 12 years’ CPTOing across Silicon Valley and London startups. We’re demanding, excitable, encouraging of experimentation, adoring of bad puns, full of smart and autonomous folks, and have built our business on a foundation of compassion and kind challenge. 💞

Sound like your cup of tea (or coffee) 🍵?

About you

We’re now hiring a Singapore‑based Head of Sales / GM to be our commercial leader for APAC - a dynamic sales leader who is STOKED to bring our AI platform to enterprise commercial real estate companies across the Asia‑Pacific region. We need an ambitious, strategic, results‑driven leader with experience closing high‑ACV deals and building sales foundations in the B2B SaaS space. You are that rare individual who excels at both running deals yourself AND laying the groundwork for future team growth.

That’s right, we need you to land us Really Big Deals across APAC. But as our Head of Sales / GM, you’re not just here to sell - you’re here to help architect and execute our entire APAC revenue strategy. Reporting directly to the CEO, you’ll collaborate closely with the Exec Team to establish our sales presence in Singapore, develop our enterprise sales motion for the region, and build the foundation for a world‑class sales organization that can scale across Asia‑Pacific.

You’re incredibly driven and have a proven track record of taking companies into new markets and achieving significant scale, with the strategic vision to see how Fifth Dimension becomes the dominant AI platform in real estate across APAC and beyond. You understand that in early‑stage companies, exceptional execution today creates the foundation for category leadership tomorrow.

You are a proven sales leader with deep AI/SaaS expertise and an entrepreneurial mindset. Your experience establishing sales operations in new markets - coupled with your ability to close complex enterprise deals and navigate diverse business cultures - makes you the perfect person to establish our APAC market presence.

More on the role

Reporting into Dr. Kate Jarvis, CEO, you will be the architect of our APAC revenue engine and the foundation of our future regional sales organization. You will own the commercial strategy for APAC, working in close partnership with the leadership team and global commercial teams to drive our ambitious growth goals. You will:

Drive Strategic Revenue Growth 🚀

• Own and exceed aggressive revenue targets, building toward significant ARR in the APAC market

• Develop and execute our enterprise sales strategy across APAC, focusing on six and seven‑figure deals with major real estate companies

• Build sophisticated sales processes that can scale from initial market entry to regional dominance

• Prove what world‑class individual sales performance looks like while establishing the foundation for future team growth

Lead Market Development 📈

• Establish Fifth Dimension as the category leader in AI‑powered real estate technology across Asia‑Pacific

• Identify and penetrate key market segments across diverse APAC markets, from large property management companies to global real estate investment firms

• Navigate and adapt to varied business cultures, regulatory environments, and market dynamics across the region

• Experiment aggressively, learn and adapt region‑specific messaging to optimize our sales motion for APAC markets

Architect Sales Excellence 🎯

• Design and implement world‑class sales methodologies, playbooks, and enablement programs tailored for APAC

• Establish the metrics, reporting, and performance management systems that will drive our regional sales organization at scale

• Create the foundation for our future APAC sales team structure and hiring plans

• Develop hyper‑efficient personal sales processes that maximize individual output and impact

Drive Product‑Market Fit Through Customer Insights 💡

• Partner closely with Solutions and Engineering teams to ensure Agent Ellie evolves based on APAC enterprise customer needs and regional requirements

• Lead complex proof‑of‑concept implementations that demonstrate transformational ROI across diverse market contexts

• Develop case studies and success stories that become the foundation of our regional marketing and sales materials

Shape Company Strategy 🧭

• Collaborate with the leadership team on APAC‑specific pricing strategy, go‑to‑market approach, and product roadmap

• Contribute to fundraising efforts with your deep market insights and customer relationships from the region

• Help define our expansion strategy across APAC markets and potentially adjacent verticals in the region

You’ll travel ~25% of the time within APAC for customer meetings and conferences, plus quarterly trips to the UK HQ/other international location for all‑company gatherings.

What we’re looking for

You’ve been a key revenue driver at a B2B SaaS company, ideally with experience selling to commercial real estate companies in APAC or establishing new market operations. You’ve proven you can both close significant deals yourself and establish the commercial foundations for future team growth. This isn’t just preferred - it’s required. We need someone who can establish the commercial foundation that will carry us to dominance across Asia‑Pacific. 🏃♀️

Must Have

• Proven sales experience at early‑stage to growth‑stage B2B SaaS companies, with a track record of exceptional individual performance and/or scaling revenue in new markets

• Enterprise sales expertise with consistent success closing six and seven‑figure deals ($100K - $1M+ ACV) and deep understanding of enterprise sales cycles

• Experience establishing sales operations or entering new geographic markets, with ability to work autonomously and build from the ground up

• Strategic thinking combined with hands‑on execution - you can develop the strategy AND close the biggest deals yourself

• Technical product expertise - experience selling complex and technical vertical products (AI/ML, deeptech, fintech, or similar) to sophisticated buyers

• Willing to travel extensively (30%+ of time) to build relationships and close enterprise deals across APAC, with regular travel to the London and New York offices

• Deep understanding of commercial real estate and the challenges facing institutional real estate companies, through direct experience or significant experience selling to the industry

• Cultural agility and experience working across diverse APAC markets with understanding of regional business practices

• A shared vision for how AI will change the world with the ability to articulate complex technical value propositions

• Located in or willing to relocate to Singapore with established or developing professional networks across APAC

• Must be a Singapore Citizen, Permanent Resident, or hold a valid work pass

• Must be open to a hybrid work schedule (2+ days per week in office)

Nice to Have

Don’t be put off applying if you can’t tick much or anything in this section - we truly believe that diverse experiences contribute to a dynamic and innovative team.

• Real estate industry experience or deep connections in the APAC property sector

• Venture‑backed startup experience through multiple funding rounds

• Experience managing or building sales teams from scratch

• Multi‑lingual capabilities (Mandarin, Japanese, or other APAC languages)

• Strong personal brand and thought leadership presence in sales or real estate tech

• Previous experience at unicorn or IPO companies during high‑growth phases

• Marketing and demand generation experience to support regional growth strategy

• Advanced CRM and sales automation expertise (HubSpot)

What we offer:

• Highly competitive salary and OTE

• Meaningful equity (on a standard vesting schedule) 📈

• Company‑sponsored medical, dental and life insurance

• Unlimited Annual Leave

• 2 week all‑company December shutdown

• Tailored support for exceptional challenges. This looks different for everyone, but can include contributions to:

  • Gender‑affirming care
  • Private specialist and scans for an injury
  • ADHD / Autism diagnosis
  • IVF
  • Therapy

• $1000 annual training budget

• $100 monthly well‑being budget - for whatever helps you feel your best 🏋️ 💅 🛍️ 🎮