Sales Enablement Manager

We're Osome - an international fintech startup making the lives of entrepreneurs easier. We help thousands of businesses kick admin, accounting and bookkeeping out of their day-to-day, so they can spend more time on what's important to them. We've developed a unique solution that combines SaaS with a human-in-the-loop approach to provide full-fledged services in real-time.

We’re experiencing rapid growth in both client base and team, which now comprises around 500 people across our offices worldwide. As we continue to scale, we’re looking for more bright minds who are excited to make a real impact by solving complex problems.

We have a growing global sales team across multiple regions, products, and jurisdictions - and the reps are delivering. But we are scaling fast and need someone who can make every seller sharper, faster, and more effective. Onboarding is ad hoc. Playbooks live in people's heads. Training happens when someone has time. That is what you are here to fix.

You own GTM enablement end-to-end, reporting directly to the VP of Sales. You will build structured onboarding, maintain living playbooks, run coaching sessions, create competitive battlecards, and sit with reps on live calls to improve how they sell. You work across AEs, SDRs, and managers in every region - flying in for team events, showing up on calls at odd hours, and doing whatever it takes to raise the bar.

This is strategic and hands-on. You partner with the VP of Sales on what the team needs to win. You collaborate with Sales, Marketing, Product, and RevOps to make sure reps have the right content, the right messaging, and the right skills for every market. And you are equally the person who records a quick training video at midnight because a new product launches tomorrow.

What To Expect

• You’ll handle real client accounts, not dummy data
• Accuracy matters — mistakes don’t hide for long
• You’ll communicate with clients and internal teams regularly

If you want to build confidence, judgement, and ownership, it will be.

What You'll Do

• Structured onboarding that gets new hires to productivity fast - across every role, region,

and product line.

• Sales playbooks: discovery frameworks, objection handling, competitive positioning, pricing guidance, and jurisdiction-specific knowledge (incorporation, accounting, tax, compliance across SG, HK, UK, UAE).
• Live coaching and ride-alongs with reps: call reviews, deal clinics, and feedback loops that directly improve conversion, deal values, and close rates.
• Competitive intelligence: what competitors do, how they price, where they win - packaged into battlecards reps actually use.
• Training programs: product deep-dives, market knowledge, skill-building workshops, and new launch enablement.
• Sales content in collaboration with Marketing: case studies, one-pagers, pitch decks, an demo scripts that reps pull into deals.
• Measuring what works: ramp time, content adoption, win rates, and deal sizes pre/post

enablement.

Who You Are

• 3+ years in sales enablement, sales training, or a hands-on B2B sales role where you built your own playbooks at a fast-scaling company.
• You have built an enablement function before - not just run one someone else designed.
• You can sell. You understand discovery, qualification, objection handling, and closing because you have done it yourself.
• You simplify complex products into clear, actionable messaging that reps use in real conversations.
• Strong content creator: battlecards, training videos, knowledge bases, pitch decks - you produce at speed.
• Scrappy and startup-minded: you travel for team events, work across time zones, show up physically when it matters, and do not wait for permission to build something the team needs.
• Data-informed: you track what works, kill what does not, and tie enablement to commercial outcomes.
• English fluency required. Mandarin strongly preferred.

You’ll leave this role better than you started. That’s the goal.

Ideal But Not Essential

• Experience in corporate services, accounting, fintech, or SaaS.
• Familiarity with HubSpot, Guru, or similar enablement tools.
• Background in B2B sales to SMEs and startups

Certifications help. Experience helps more. Attitude matters most.

Why Osome

• A growing global sales team that is ready to be leveled up - you are not enabling from zero,you are accelerating what works.
• Direct partnership with the VP of Sales on commercial direction and what the team needs to win.
• Global scope: work across markets, cultures, and teams spanning every timezone.
• Every rep you make better drives revenue - your impact is directly measurable.
• Startup energy with real revenue and product-market fit across 4 markets.
• Direct access to leadership and fast decision-making - no layers.
• Competitive compensation with uncapped, performance-based incentives.

Our Benefits

• Multi-cultural environment to enhance your global perspective.
• Learning opportunities and mentorship from peers and leaders.
• An agile working model focused on goals and performance.
• Remote working arrangement.
• Office laptop and other equipment provided.

Equal Opportunity Statement

At OSOME, creating a culture where individuals of all backgrounds feel comfortable really matters.

Everyone who applies will receive fair consideration for employment. We do not discriminate based upon race, colour, religion, sex, sexual orientation, age, marital status, gender identity, national origin, disability, or any other applicable legally protected characteristics in the location in which the candidate is applying. We want to ensure that we represent the diversity of talent in the society we live in today.

If you have any accessibility requirements that would make you more comfortable during the application and interview process, please let us know so that we can support you.

We believe that entrepreneurs are society's problem solvers. They see opportunities in complexities and drive us towards progress. Osome doesn't want entrepreneurs to be distracted from the important task of searching for the best solutions. By letting us handle all the routine tasks, entrepreneurs can focus on driving their business forward.