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Head of Customer Success

Parallel Systems is building autonomous, battery-electric rail vehicles to modernize freight transportation. We are seeking a Head of Customer Success to own the full customer lifecycle after contract signature, including implementation, onboarding, training, adoption, and expansion.

This is a senior, high-ownership role for someone who can manage large enterprise customers, lead complex hardware and software deployments, and build trusted relationships with executives and operators. Our customers are making major operational decisions around first-of-a-kind technology, and this person will be responsible for making sure those customers successfully deploy, adopt, and expand with Parallel.

We are looking for someone who has supported large enterprise accounts, ideally with $5M to $10M+ deal sizes, and can operate comfortably with C-suite leaders, VP-level operations stakeholders, field teams, and internal engineering teams. The right person brings executive presence, operational depth, and the ability to build a repeatable customer success function as Parallel scales commercial deployments.

This role will require up to 50% travel to customer and deployment sites.

Responsibilities:

• Secure significant follow-on revenue opportunities from existing customers
• Own the full post-sale customer lifecycle, including implementation, onboarding, training, adoption, account health, and expansion.
• Lead complex customer implementations involving hardware, software, operational workflows, field teams, and customer infrastructure.
• Serve as the primary customer success leader for enterprise accounts, building trusted relationships with C-suite executives, VP Operations leaders, technical stakeholders, and field operators.
• Translate signed commercial agreements into clear implementation plans, milestones, timelines, risks, responsibilities, and success criteria.
• Partner closely with Sales, Product, Engineering, Operations, and Deployment teams to ensure customers are successfully launched and supported.
• Drive customer readiness across training, operational procedures, integration requirements, change management, and post-launch support.
• Identify and drive expansion opportunities, including additional vehicles, new sites, broader network adoption, and deeper operational integration.
• Represent Parallel in executive meetings, customer business reviews, onsite visits, industry events, and strategic account conversations.
• Build customer success playbooks, implementation processes, account health frameworks, escalation paths, and reporting rhythms.
• Track customer adoption, risks, sentiment, operational readiness, and expansion potential across key accounts.
• Act as the voice of the customer internally, ensuring customer needs, blockers, and feedback are clearly communicated to Product, Engineering, Operations, and leadership.
• Help define the long-term Customer Success organization, including future hiring, team structure, metrics, and operating model.

What Success Looks Like:

• Within 30 days: you have ramped on Parallel's product, customers, commercial commitments, deployment model, and internal workflows. You have built relationships with Sales, Product, Engineering, Operations, and leadership, and are beginning to map the customer lifecycle from contract signature through successful deployment.
• Within 60 days: you are actively owning customer implementation plans, building executive and operational relationships, identifying key risks, and creating the first version of Parallel's customer success operating model. You are bringing structure to post-sale execution and helping cross-functional teams stay aligned around customer outcomes.
• Within 90 days: you are independently driving customer success for key enterprise accounts, leading implementation and expansion conversations, managing escalations, and creating repeatable processes that can scale across future deployments. You are clearly establishing the foundation for Parallel's Customer Success function.

Requirements:

• 8+ years of experience in customer success, implementation, account management, deployment, post-sale operations, or a related customer-facing function.
• Experience managing large enterprise customers with complex buying committees and high-value commercial relationships.
• Track record working with $5M to $10M+ enterprise deals, strategic accounts, or major implementation programs.
• Strong executive presence with the ability to engage credibly with C-suite leaders, VP-level operators, technical stakeholders, and field teams.
• Experience leading complex implementations that require cross-functional coordination, customer change management, and operational execution.
• Ability to manage both strategic customer relationships and tactical deployment details.
• Strong commercial instincts with experience identifying and supporting upsell, expansion, renewal, or broader account growth opportunities.
• Comfort working with technical products that include some combination of hardware, software, integrations, infrastructure, operations, logistics, or field deployment.
• Strong communication skills, including executive updates, customer briefings, escalation management, and internal alignment.
• Ability to operate in an early-stage environment where playbooks need to be built while work is already in motion.
• Willingness to travel for customer meetings, deployment work, executive events, onsite implementation, and industry engagements as needed.

Preferred Qualifications:

• Experience in transportation, logistics, rail, supply chain, industrial automation, autonomy, robotics, hard tech, or enterprise infrastructure.
• Experience with products that require both hardware deployment and software implementation.
• Experience working directly with operations teams, field teams, or customers in safety-critical or operationally complex environments.
• Experience building a Customer Success, implementation, or post-sale account function from the ground up.
• Experience supporting expansion programs where customers grow from an initial deployment into broader commercial adoption.
• Experience owning or contributing to customer incentive plans, expansion targets, or account growth metrics.
• Experience representing a company at customer events, executive forums, industry conferences, or strategic business reviews.

Compensation:

• The expected salary for this role is between $180,000-$200,000 plus incentive pay, with an on-target expectation of $250,000-$300,000.