Customer Success Manager (Retention Specialist) - Bobtail
Does Bobtail sponsor H-1B visas?
Check real filing data, salaries & approval rates on VisaTalentUSA
Job Description
Remote customer service roles on HireSkys cover support, technical support, chat support, and community management. Check the listed hours, languages, and support tools before applying.
Key Skills Required
Master these to land this role
Want to know if you're a match for this job?
About Bobtail: Bobtail is dedicated to increasing happiness by eliminating inefficiencies in the supply chain. We envision a supply chain without friction, fraud, waste, and abuse where companies succeed based on the value they create.
We work in a unique way at Bobtail, where we value teams over individuals and encourage experimentation and iteration to constantly improve. Teams are given flexibility in working towards a shared purpose and the freedom to decide how they will accomplish their goals.
If you are an out-of-the-box thinker who takes a proactive approach in collaborating with others to solve problems and achieve goals, we would love to talk to you.
The things we value:
- Mission
- Teams over individuals
- Collaboration
- Communication
- Iteration
- Experimentation and failing fast
- Initiative and solutions-oriented approach
- Documentation
- Data
- Mental health and work-life balance
- Diversity
- Transparency
You should apply if you are/have:
- Sales skills
- 1-3 years of experience in SaaS and B2B environments
- Excellent English and Punjabi proficiency – written and verbal communication skills
- 1-3 years of proven experience in retention
- A Bachelor’s Degree in relevant fields (business, marketing, customer service)
- Prior US trucking industry experience is a plus
Qualities and Attributes:
- Active listening skills
- Good time management
- Great communication skills
- Persuasion ability
- Compassion
- Critical thinking and problem-solving skills
- Good organizational skills
- Attention to detail
- Patience and resilience
- Willingness to go above and beyond
- Data orientation
- Ethical conduct
- Collaborative attitude
- Cultural sensitivity
- Adaptability
You will be responsible for:
- Customer relationship management by maintaining long-lasting relationships, monitoring customer adoption and satisfaction through customer outreach.
- Collaborating with team members to decrease churn, increase retention rates, and improve brand loyalty.
- Troubleshooting problems; addressing customer issues, complaints, and dissatisfaction promptly and coordinating with relevant departments to find solutions and follow up.
- Identifying at-risk customers, developing, and implementing retention strategies.
- Collecting customer feedback to provide insights for product owners and marketing teams to enhance our service.
- Monitoring assigned emails (personal and terminations) to address requests in a timely manner.
- Documenting customer interaction, feedback, and resolution in the CRM, and regularly reporting on retention efforts and outcomes.
- Identifying opportunities to upsell or cross-sell. Providing information about complementary offers and/or new products.
- Maintaining an in-depth understanding of our products, services, and value proposition to educate customers.
Benefits:
- Monthly Mental Break Day
- Paid Time Off
- Work from home (or wherever)
- Parental leave
How would you rate this job post?
See what other professionals think about this role.
How applying works on HireSkys
- 1.Click Apply. You go to the application — the employer's own page or form, or the HireSkys apply flow — and submit your profile as the employer asks.
- 2.The employer reviews. Shortlisting is done by the employer, not by HireSkys, so the timeline and next steps come from them.
- 3.Hear back directly. If shortlisted, the employer contacts you directly. Applying through HireSkys is free for jobseekers — never pay for a job application.
Similar Opportunities
More Openings at Bobtail
Explore Top Companies in this Space
Kiwi Crédito
Fintech / Digital Lending / Consumer Finance / Financial Services
Skip Loans
Specialized Finance / Financial Services
First Entertainment Credit Union
Finance / Credit Unions / Financial Services / Entertainment Industry Support
Above Lending
Consumer Finance / Personal Loans / Financial Services / Debt Consolidation
Bobtail
View Company ProfileBobtail (operating at bobtail.com) is a financial services platform engineered for the trucking industry, specializing in cash flow optimization and operational cost reduction. While freight carriers often face inefficiencies in supply chain financing, Bobtail streamlines these challenges with a zero-fee fleet card and transparent factoring solutions. The company’s offerings include same-day funding and no hidden fees, addressing the liquidity gaps that hinder growth for small to mid-sized trucking businesses. Under the hood, Bobtail leverages digital invoicing and financing tools to accelerate payments while maintaining competitive rates. This allows carriers to focus on their core operations—transportation and logistics—without the administrative burdens of traditional financing. Backed by $155 million in total funding, including a $100 million debt financing arrangement with Clear Haven Capital, Bobtail has scaled rapidly to support over $1 billion in funded invoices, reshaping how truckers manage their finances.
Safety First
- Never pay for a job application.
- Do not share sensitive bank info.
- Verify the client before starting work.

