Technical Services

Location: Remote (Pacific/Mountain)

About Wholesail

• Founded: 2018
• Website: https://paywholesail.com
• Locations: San Francisco (HQ); Beijing
• Funding: Series A $35M (Foundry Group, Thomvest, Flexport, Gokul Rajaram et al)
• Company Size: 40 total (20 in eng and product; ~20 GTM)

U.S. wholesalers extend over $3 trillion in trade credit every year—yet 40% of invoices still go past due. Wholesail’s credit and payment platform turns 40-day pay cycles into 30 days, freeing cash for growth. Today, Wholesail empowers over 400+ wholesalers and 100,000 of their buyers to manage payment risk without compromising customer relationships or growth through its suite of payment, credit and customer onboarding products.

Wholesail was founded by serial entrepreneurs who sold their last two startups to OpenTable. The founding team has worked together for over a decade as a tightly knit group of product, engineering and go-to-market leaders. The company is well-funded, with backing from a half dozen VC firms and more than 20 angel investors with backgrounds in fintech and SMB marketplaces including early team members from Stripe, Square, Dropbox, Yelp and OpenTable.

Your Impact:

You keep daily operations accurate and on time. As the first line of Technical Services, you run scheduled reports, triage support cases, and communicate clear updates by email or phone. You'll wear many hats and play a pivotal role in helping support our customers.

When needed, you look a level deeper: review third-party tools and logs, reproduce issues, and file concise bug reports so engineering can act.

Each resolved case strengthens the system - better playbooks, fewer repeats, and steadier payment operations customers can trust.

What You’ll Do:

• Deliver white-glove support: Resolve customer questions quickly and empathetically via email, phone, and video.
• Detect & decide: Trust your gut - when logs, queries, or a “something’s off” feeling point to trouble, investigate, fix, or escalate with clear context.
• Hard-proof your work: Double-check reports and customer comms before sending - QA is part of the job, not an afterthought.
• Own daily operations: Generate reports, triage tickets in Salesforce Service Cloud, and execute scheduled tasks without missing a beat.
• Troubleshoot integrations: Combine logs, spreadsheets, and accounting data to pinpoint issues and solve problems.
• Champion product quality: File clear bug reports and share insights that drive feature improvements.
• Document and scale: Create SOPs that empower the team and improve time-to-resolution as we grow.

What You Bring (Must-Have):

• 1+ year in a technical or fintech customer-support role.
• Customer-first instinct: You do what’s right for the customer—even if that means saying “I don’t know yet” and digging in.
• Critical thinker with judgment: You know when to tackle an issue solo and when it’s smarter to loop in some help.
• Self-directed learner: New tool? New workflow? You figure it out, take notes, and keep going.
• Fluency with support tools like Google Workspace, remote-desktop tools, and ticketing systems (Salesforce Service Cloud preferred).
• Meticulous attention to detail and an uncanny ability to prioritize when urgency strikes.
• Clear, concise communication skills - comfortable translating technical jargon into plain language for customers and colleagues.
• A learner’s mindset and a bias for action.

Bonus Points:

• Prior experience in fintech, wholesale, or payments.
• Startup chops - comfort thriving in fast-changing environments.
• Hands-on familiarity with accounting software (QuickBooks, NetSuite, Sage 50).
• Passion for restaurants, hospitality, or food distribution.

Benefits & Perks:

• Competitive salary: $50k–$55k base, plus equity.
• Comprehensive coverage: Medical, dental, vision, short-term disability, and 401(k).
• Time to recharge: 15 PTO days, 5 paid sick days, and company holidays.
• Remote set-up: $2,000 stipend for your home office and $50/month towards internet.