Sales Development Representative (SDR)

About High Five

Hiring internationally should be much easier than it is.

Companies looking for talent across Southeast Asia still have to choose between doing everything themselves, hiring expensive internal recruiting teams, or paying traditional agencies large success fees.

High Five is building a better model.

We combine human recruiters, AI agents, and software to help companies find, assess, and hire great talent across borders. Our recruitment subscription gives companies a full-service recruiting team for a flat monthly fee, while our Employer of Record service helps them legally employ and pay people in markets where they do not have their own entity.

Today, we work with companies across multiple international markets and help them build teams across Southeast Asia.

We're still a small team, which means good ideas get implemented quickly, individual performance is visible, and the people who join now will have a meaningful role in shaping how the company grows.

About the Role

You'll be responsible for starting conversations with companies that could become High Five customers.

This is not a role where success means sending thousands of generic emails.

Your job is to understand who we should be speaking to, find the right people inside those companies, write messages that actually deserve a response, and consistently turn outbound prospecting into qualified sales meetings.

You'll primarily sell two High Five products:

• Our recruitment subscription, helping companies hire talent without traditional agency success fees
• Our Employer of Record service, helping international companies employ and pay people compliantly in markets where they do not have a local entity

You'll work directly with the CEO and have significant ownership over how outbound is executed.

Role and Responsibilities

• Use signals such as hiring activity, international expansion, open roles, new market entry, and company growth to identify companies that are more likely to need High Five
• Build targeted prospect lists of companies that match High Five's ideal customer profile across international markets
• Identify the right decision-makers, including founders, CxOs, Heads of HRs, Talent leaders, and other relevant stakeholders
• Research prospects before outreach so messages are relevant and accurate
• Write personalized cold emails, LinkedIn messages, and follow-ups designed to start genuine conversations
• Run outbound campaigns across email and LinkedIn
• Test different industries, personas, geographies, offers, and messaging angles to improve conversion
• Keep prospect and campaign data organized and up to date
• Track outreach performance and understand where prospects drop out of the funnel
• Consistently generate qualified sales meetings and build a healthy pipeline every month.

The Tools You'll Use

You'll work with tools such as:

• LinkedIn Sales Navigator
• Instantly
• Apollo
• Airtable
• ChatGPT, Gemini, Claude, or other LLMs/agentic tools
• Other prospecting and sales tools we adopt as the company grows

We care less about whether you have used every exact tool before and more about whether you can learn new tools quickly and use them intelligently.

AI should make you better at your job, not replace your judgment.

What Success Looks Like

Within your first 90 days:

• You understand High Five's products, customers, and ideal customer profiles well enough to identify strong prospects independently
• You can build high-quality prospect lists without needing someone to check every account
• You are consistently running outbound campaigns across email and LinkedIn
• Your research and outreach contain very few avoidable mistakes
• You understand which messages, personas, industries, and markets are converting — and which are not
• You are generating qualified meetings consistently and are clearly progressing toward your target
• You are bringing ideas to the CEO about how we can improve outbound rather than simply executing instructions
• When a campaign underperforms, your instinct is to investigate, experiment, and improve it

Qualifications

• 2–5 years experience doing outbound B2B sales, business development, or sales development
• Proven experience prospecting through cold email and LinkedIn
• Experience selling or prospecting to B2B customers outside Indonesia (Singapore, HK, Australia, USA, Canada, UK and more)
• Excellent written and spoken English
• Comfortable researching companies, industries, and individual prospects
• Strong attention to detail — names, companies, job titles, personalization, CRM data, and follow-ups need to be accurate
• Comfortable working with numbers and understanding basic outbound metrics such as reply rates, meeting rates, conversion rates, and pipeline
• Able to manage your own workload in a remote environment
• Comfortable with flexible working hours (early mornings and late nights) when international prospects require it

The Kind of Person Who Will Do Well Here

• You care about results and look for ways to improve your performance without being asked.
• You consistently follow through. If you commit to doing something, it gets done without constant reminders.
• You're highly detail-oriented and take pride in getting the small things right.
• You're resilient and persistent — rejection doesn't discourage you or stop you from following up.
• When something doesn't work, your first instinct is to understand why and improve it, rather than look for excuses.
• You ask good questions, challenge assumptions, and actively look for patterns that can make outbound more effective.

Where You Might Be Coming From

You might currently be:

• An SDR, BDR or AE at a SaaS or technology company
• Doing outbound sales for an agency, recruitment company, or professional services business
• Selling internationally from Indonesia or elsewhere in Southeast Asia
• Working at a startup where you had to build your own prospect lists rather than being handed perfectly qualified leads
• Running email and LinkedIn outreach campaigns for international B2B customers

Your title matters less than whether you can show us that you know how to create qualified sales conversations.

Hiring Process

1. Application Review
2. 15-Minute Intro Call With the CEO
3. Take-Home Exercise
4. Take-Home Walkthrough
5. Offer

Hit the apply button and see you at the call!