Breaking into Remote Customer Success – Background in Sales, Moving Global in 2026. Looking for Advice.

Hi everyone,

I’m currently planning my transition into a fully remote career and would really appreciate some advice from people who already work remotely.

Here’s a short overview of my background:

• 3 years apprenticeship in the insurance sector (Germany) working as a customer advisor in field sales (client consulting, needs analysis, CRM documentation, relationship management) • 1 year in wholesale/retail B2B sales as a customer manager responsible for account development and maximizing customer potential • 8 months in Greece (Crete) working in a 5-star luxury hotel environment (guest relations + shop staff). Daily English usage, international clientele, service-focused role • ~1 year family caregiving (full-time) • 7 months marketing & social media marketing training (certificate program) • Since Jan 2025: Field Sales & Customer Relationship Manager in the food/retail sector, handling new customer acquisition + close management of key accounts (“A clients”), long-term relationship building and upselling 

My long-term goal:

By 2026/early 2027 I want to work fully remote, globally location-independent (Asia, Europe, South America etc.) with a target income of around €1,500–2,000 base + performance bonuses initially.

I’m currently focusing on moving into Customer Success / Customer Support (non-voice or low-call) roles because:

• I already have strong customer-facing and relationship management experience • I want to avoid aggressive outbound sales pressure • I prefer chat/email-based communication while continuing to improve my spoken English 

My current plan:

• Learn and practice HubSpot CRM, Zendesk/Intercom-style ticket systems • Improve professional written English for support/customer success communication • Optimize my LinkedIn profile and CV for international remote roles • Start applying to remote-first SaaS/startup companies later this year 

Questions for those who already made the jump:

1. Is Customer Success / Support a good entry path into the remote world with my background? 2. What skills or tools helped you the most when landing your first remote role? 3. Would you recommend startups or more established remote companies for the first job? 4. Any mistakes you would avoid if you had to start again? 

Thanks a lot in advance – I really appreciate any honest insights or experiences.