Our board wanted us to "expand into Asia."
I asked which countries. They said "all of them—it's a massive market opportunity."
That statement revealed a fundamental misunderstanding about Asia-Pacific B2B markets: treating "Asia" as a single market is like treating "Europe and the Middle East and Africa" as a single market. The geographic proximity doesn't create market homogeneity.
Japan operates nothing like Indonesia. Singapore's business culture is completely different from China's. South Korea's procurement processes bear no resemblance to Thailand's.
We learned this the expensive way.
We tried to launch simultaneously in Japan, Singapore, and Australia with one "Asia-Pacific strategy." We spent $800K across nine months and acquired exactly three customers—all in Singapore.
Then we rebuilt our approach as a Singapore-first beachhead strategy, using success in Singapore to expand methodically into other Asian markets.
Two years later, APAC generated $4.8M ARR across eight countries. But it started with admitting that "expand into Asia" isn't a strategy—it's a geographic fantasy.
Why Singapore Became Our Beachhead (and Should Be Yours)
When we analyzed why our pan-Asian launch failed but our Singapore customers succeeded, a pattern emerged:
Singapore customers:
- Responded to English-language marketing
- Signed contracts with minimal legal customization
- Operated on similar business calendars as Western companies
- Used payment infrastructure compatible with our billing systems
- Made purchasing decisions on 2-3 month timelines similar to US
Japan customers we pitched:
- Needed Japanese-language sales process and materials
- Required extensive contract customization for Japanese business law
- Operated on fiscal years ending March 31 (different from Western December 31)
- Used local payment rails incompatible with our systems
- Required 6-12 month relationship-building before discussing business
We decided to master one Asian market completely before expanding to others. Singapore became our beachhead for specific reasons:
English as business language: Singapore's business community operates in English. No translation barrier for sales, support, or documentation.
Western-compatible business practices: Singapore adopted Anglo-American business frameworks. Contracts, procurement processes, and corporate governance resemble Western models.
Regional headquarters concentration: Multinational companies use Singapore as their Asia-Pacific headquarters. Win a Singapore-based APAC team, and you get access to their regional operations.
Financial infrastructure: Singapore's banking and payment systems integrate with Western payment processors. No need to build local payment infrastructure.
Timezone overlap with Australia: Singapore is close enough in timezone to Australia that one sales team can cover both markets.
Gateway to Southeast Asia: Success in Singapore creates credibility for Malaysia, Thailand, Indonesia, and Vietnam expansion.
We restructured our Asia strategy: dominate Singapore first, then use Singapore as the launch pad for the rest of Asia.
The Sales Motion That Works in Singapore (Relationship Speed-Dating)
American B2B sales: meet the buyer, pitch the product, negotiate, close. Total time: 1-4 meetings over 1-3 months.
Singapore B2B sales follows a different pattern that I'd describe as "relationship speed-dating."
Singaporean buyers want to establish a relationship before they'll seriously evaluate your product. But unlike Japan (where relationship-building takes months of dinners and introductions), Singapore compresses this into a faster, more efficient process.
The pattern we learned:
Meeting 1: Introductory coffee (30-45 minutes) Not a sales meeting. This is mutual evaluation. The buyer is assessing: Are you credible? Do you understand their market? Are you committed to Singapore or just testing the waters?
Don't pitch. Have a conversation about their business, their challenges, and whether there might be fit.
Meeting 2: Exploratory discussion (45-60 minutes) Now you can discuss your solution, but frame it as exploration, not sales. "Based on our last conversation, here's how companies similar to yours have approached this problem. Would this be relevant for your situation?"
Meeting 3: Formal presentation (60-90 minutes) This is your actual pitch, but only after the relationship foundation is established through meetings 1-2.
We retrained our Singapore sales team to stop trying to close in the first meeting. The American "always be closing" mentality failed because Singaporean buyers interpreted aggressive closing as lack of relationship respect.
Once we slowed down and invested in relationship building—while still moving faster than Japan or Korea—our close rate improved from 15% to 52%.
Why "Asia-Pacific Pricing" Is a Mistake
We launched with one pricing model for all of APAC: the same USD pricing we used in the US, assuming we'd handle currency conversion.
This failed for different reasons in different markets:
Singapore: USD pricing was fine, but buyers wanted SGD-denominated contracts for budgeting certainty.
Australia: Demanded AUD pricing. Refused to accept currency risk.
Japan: Needed JPY pricing with specific invoice formatting required by Japanese accounting standards.
India: USD pricing put us far above local competitors. Needed INR pricing at India-specific price points (30-40% below USD equivalent).
We learned that "Asia-Pacific" isn't a pricing region—each country needs country-specific pricing strategy:
Developed markets (Singapore, Australia, Hong Kong): Can support Western-equivalent pricing but need local currency denomination.
Japan and South Korea: Need local currency but premium pricing (often 10-20% above Western prices because enterprise buyers expect premium for foreign software).
Emerging markets (India, Thailand, Indonesia, Vietnam): Need substantially lower price points (30-50% below Western pricing) to compete with local alternatives.
China: Requires completely different business model (often local partnership or JV) due to regulatory requirements and buyer preferences.
We built country-specific pricing:
- Singapore: SGD pricing at Western equivalent rates
- Australia: AUD pricing at Western equivalent rates
- Japan: JPY pricing at 10-15% premium
- India: INR pricing at 60% of Western rates
- Southeast Asia: USD pricing negotiable based on company size
This pricing localization was critical. When we tried to charge an Indian mid-market company the same price as a Singaporean enterprise, we lost every deal.
The Partner Strategy That Unlocked Southeast Asia
We could sell direct in Singapore and Australia (English-speaking, Western business practices). Every other Asian market required local partners.
Not because we couldn't hire local teams—because buyers preferred working with local partners over direct foreign vendors.
A Thai prospect told me: "Your product is good. But if I have implementation issues or need support, I don't want to deal with time zones and language barriers. I want a Thai partner who understands my business and can help me in my language."
We built a multi-tier partner strategy:
Singapore direct sales: Our own team selling to Singapore-based companies and regional headquarters.
Country-specific implementation partners: Local consulting/services firms in each market who sold our platform bundled with their implementation services.
Regional system integrators: Large SIs with pan-Asian presence (Accenture, Deloitte, NTT Data) who recommended our platform for multi-country deployments.
Technology alliances: Local technology vendors (cloud providers, local SaaS companies) who co-sold with us.
The partner economics varied by country:
Developed markets: 20-25% partner margin Emerging markets: 35-40% partner margin (higher margin because partners needed to invest more in local sales and support)
This partner-heavy model reduced our margins but gave us market access we couldn't build ourselves. A local Thai partner could sell in Thailand far more effectively than our direct team ever could.
For companies building multi-country expansion strategies in Asia, platforms like Segment8 provide regional partner framework templates that help structure country-specific partnerships while maintaining consistent positioning across markets.
What We Got Wrong About Japan (The Market We Couldn't Crack)
Japan is the second-largest economy in Asia. We assumed it would be a major revenue source.
After two years of trying, Japan represented 3% of our APAC revenue.
Here's why Japan is uniquely difficult for foreign B2B software companies:
Relationship requirements: Japanese business culture requires extensive relationship-building before business discussions. Buyers want multiple in-person meetings over months before they'll consider a purchase.
Decision-making timeline: Even after relationship establishment, decision cycles run 9-12 months for enterprise purchases. Consensus-building across departments and hierarchy levels takes time.
Local presence expectation: Japanese buyers strongly prefer vendors with Japanese legal entities, Japanese employees, and Japanese office presence. Being a "foreign company with Japan partners" isn't equivalent to being a Japanese company.
Language barrier: Despite many Japanese businesspeople speaking English, complex software evaluation requires Japanese-language materials, sales process, and support.
Price expectations: Japanese buyers often expect premium pricing from foreign vendors (which worked in our favor) but also expect premium service levels (24/7 Japanese-language support, which we couldn't provide).
Customization demands: Japanese customers wanted significant product customization to match their specific workflows. Our SaaS model didn't accommodate heavy customization.
We tried three approaches in Japan:
Approach 1: Direct sales with Japanese-speaking American team. Failed. Buyers wanted native Japanese sellers.
Approach 2: Japanese implementation partner. Partial success but slow. Partner could sell but lacked technical depth.
Approach 3: Joint venture with Japanese software company. Most successful but expensive and complex.
Our lesson: Japan requires full market localization—Japanese entity, Japanese employees, Japanese product customization—that may not be economically viable until you have significant APAC revenue from easier markets.
We decided to defer serious Japan investment until we hit $10M APAC ARR from Singapore, Australia, and Southeast Asia. Then we'd have the resources to invest properly in Japan.
The India Strategy That Worked (After Three Failed Attempts)
India looked perfect on paper: 1.4 billion people, fast-growing economy, strong technology adoption, English-speaking business community.
We launched in India three times and failed three times before finding an approach that worked.
Failed Approach 1: Western pricing with India-based sales team
We hired Indian sales reps but charged Western prices. We lost every deal to local Indian competitors pricing 60-70% below us.
Failed Approach 2: Drastic price reduction (80% off Western pricing)
We cut prices to compete with local alternatives. We won customers but couldn't cover the cost of serving them. Economics didn't work.
Failed Approach 3: India as pure partner channel
We tried to sell entirely through Indian partners. Partners wanted custom features and intensive support we couldn't provide profitably.
Successful Approach 4: India-specific product tier + partner channel + enterprise direct
We built a separate product tier for India with reduced functionality but sufficient for Indian mid-market needs. Priced at 40% of Western pricing.
Partner channel sold this tier to mid-market customers. Margins were thin but volume made up for it.
Our direct team focused only on Indian enterprises willing to pay near-Western prices for full product capability.
This segmented approach let us serve the Indian market profitably:
- Mid-market: simplified product, partner-sold, volume-based economics
- Enterprise: full product, direct-sold, premium pricing
The Cultural Differences That Broke Our First Deals
Asian business culture isn't monolithic, but we made American assumptions that failed across multiple Asian markets:
Assumption: Decision-makers are obvious
In American companies, you can usually identify the decision-maker (VP of Sales, CTO, etc.). In many Asian companies—especially family-owned businesses common in Southeast Asia—the real decision-maker might be the founder's son, a family member not in the org chart, or a trusted advisor outside the company.
We'd navigate the official procurement process only to have deals die because "uncle needs to approve" and we'd never met uncle.
Assumption: Written contracts are final
In Western business, signed contracts are definitive. In some Asian markets, contracts are starting points for ongoing relationship negotiation.
We'd sign a contract, then customers would request modifications, payment term changes, or additional services "because we're partners now."
Assumption: Direct communication is professional
American business culture values direct communication. Many Asian cultures value indirect communication that preserves relationship harmony.
We'd ask "Will you sign this quarter?" Buyers would say "We're very interested" (meaning no, but wanting to preserve the relationship). We'd forecast the deal. It wouldn't close.
We learned to interpret indirect communication signals and ask questions that allow buyers to communicate indirectly without embarrassment.
Assumption: Contracts don't require relationship maintenance
In the US, once you close a customer, the relationship shifts to customer success teams. In Asia—especially Singapore, Japan, Korea—the salesperson who closed the deal is expected to maintain the relationship even after handoff.
Customers felt abandoned when our sales reps stopped engaging post-sale. We restructured our sales model to keep reps involved in relationship maintenance even after implementation.
What Worked: The Sequential Market Entry Strategy
Instead of pan-Asian launch, we built a sequential strategy:
Year 1: Singapore beachhead
- Establish Singapore entity
- Build Singapore customer base and references
- Develop APAC team and operations
Year 2: Singapore + Australia + easy Southeast Asia
- Expand to Australia (similar business culture to Singapore)
- Add Malaysia and Thailand via partners (geographic proximity to Singapore)
- Build APAC case studies and proof points
Year 3: Emerging Southeast Asia + India mid-market
- Add Indonesia, Vietnam, Philippines via partners
- Launch India mid-market tier
- Grow APAC team supporting multiple markets
Year 4+: Japan and China (requires major investment)
- Only after APAC revenue justifies full localization investment
This sequential approach let us learn from each market before expanding to the next. Each new market was easier because we had regional proof points and experienced team members.
The Uncomfortable Truth About Asian Market Expansion
Asia-Pacific is the highest-growth region for B2B software. It's also the most complex, expensive, and time-consuming region to enter.
Each country requires:
- Local language capabilities (except Singapore, Australia)
- Local payment and billing infrastructure
- Country-specific legal and compliance
- Cultural adaptation of sales and marketing
- Local partnership or entity establishment
The cost to enter one Asian market properly is similar to entering all of Europe. But Europe is somewhat culturally similar. Asian markets are radically different from each other.
Our data after three years:
Customer acquisition cost:
- Singapore: $8K (similar to US)
- Australia: $9K
- Japan: $45K (and still unprofitable)
- India: $3K (mid-market tier)
- Southeast Asia: $6K (partner-led)
Average contract value:
- Singapore: $65K annually
- Australia: $70K annually
- Japan: $120K annually (premium pricing)
- India: $18K annually (mid-market tier)
- Southeast Asia: $35K annually
The economics work in some markets (Singapore, Australia) and don't work yet in others (Japan). You need portfolio economics across multiple Asian markets to make the regional investment worthwhile.
What doesn't work in Asian B2B expansion:
- Treating "Asia" as one market
- Simultaneous multi-country launch
- One pricing model for all countries
- American sales tactics (aggressive closing)
- Direct sales without local partners in non-English markets
- Ignoring relationship-building expectations
What works:
- Singapore-first beachhead strategy
- Sequential country entry based on market readiness
- Country-specific pricing and product tiers
- Relationship-building before selling
- Partner-led expansion in non-English markets
- Cultural adaptation of sales, support, and product
- Patience with long decision cycles in Japan, Korea
Asian market expansion requires accepting that growth will be slower and more expensive than other regions, but the long-term market opportunity justifies the investment if you're willing to do it properly.
The companies that succeed in Asia are the ones willing to invest in deep localization, patient relationship-building, and country-by-country strategies.
The companies that fail are the ones who try to run Western playbooks in Asian markets or try to cover too many markets too quickly without proper localization.
We succeeded by starting small (Singapore only), proving the model, then expanding methodically. Three years in, APAC is our fastest-growing region. But it required abandoning our "launch everywhere at once" instincts and building for Asian market realities.