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Bobtail
Customer Service 4h ago

Customer Success Manager (Retention Specialist) - Bobtail

Bobtail
United StatesUnited States
Full-time
Not Disclosed
Mid-Level
VT

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Job Description

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Key Skills Required

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Customer Support35 minFree Trial ✨
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CRMRetention SpecialistCustomer Feedback AnalysisCustomer Relationship Management

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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

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Bobtail (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.

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Customer Success Manager (Retention Specialist) - Bobtail at Bobtail | HireSkys