Head of Customer Success

About Parallel Systems

Parallel Systems is revolutionizing freight transportation by developing autonomous, battery-electric rail vehicles aimed at shifting segments of the $900 billion U.S. trucking industry onto rail. Their cutting-edge technology emphasizes safer, cleaner, and more efficient logistics solutions that promise to reshape global freight movement.

Role Overview

We are seeking an experienced Head of Customer Success to oversee the entire customer journey after contract signing. This includes responsibilities such as implementation, onboarding, training, driving adoption, and expanding customer relationships. This pivotal senior position demands someone adept at handling large enterprise clients, leading complicated hardware and software rollouts, and cultivating trusted partnerships with executives and operational teams.

Key Responsibilities

• Maximize additional revenue streams from existing customers by identifying and pursuing follow-on opportunities.
• Manage the comprehensive post-sale customer journey encompassing implementation, onboarding, training, adoption monitoring, account health assessments, and growth initiatives.
• Lead multifaceted installations integrating hardware, software, operational procedures, field personnel, and customer infrastructure.
• Serve as the principal customer success contact for enterprise accounts, forging strong relationships with C-suite executives, VP operations leaders, technical stakeholders, and field operators.
• Convert commercial contracts into detailed execution plans outlining milestones, schedules, risks, responsibilities, and success metrics.
• Collaborate closely with Sales, Product, Engineering, Operations, and Deployment teams to ensure smooth launches and ongoing support.
• Facilitate customer readiness by managing training programs, operational workflows, integration prerequisites, change management, and post-launch assistance.
• Spot and promote expansion possibilities including additional vehicle deployments, new sites, wider network adoption, and deeper operational integration.
• Represent Parallel Systems at executive meetings, customer business reviews, onsite engagements, industry events, and strategic account discussions.
• Develop and refine customer success playbooks, implementation workflows, account health frameworks, escalation procedures, and reporting cycles.
• Monitor customer adoption levels, potential risks, sentiment, operational preparedness, and opportunities for expansion across key accounts.
• Act as the customers' advocate internally to ensure their needs, challenges, and feedback are communicated effectively to Product, Engineering, Operations, and company leadership.
• Contribute to defining the long-term Customer Success department structure, including future recruitment, team organization, metrics, and operational models.

Success Milestones

• Within 30 days: Gain in-depth understanding of Parallel's products, customers, commercial commitments, deployment processes, and internal operations. Build relationships across teams and start mapping the full post-contract deployment lifecycle.
• Within 60 days: Take ownership of customer implementation plans, forge executive and operational contacts, identify risks, and formulate the initial customer success operating model. Implement structure to post-sale activities and align cross-functional teams on customer outcomes.
• Within 90 days: Independently lead customer success initiatives for major enterprise accounts, guide implementations and expansion discussions, manage escalations, and establish scalable repeatable processes building Parallel's Customer Success foundation.

Candidate Requirements

• Minimum 8 years of experience in roles such as customer success, implementation, account management, deployment, or related post-sale functions.
• Proven experience managing sizeable enterprise accounts involving complex decision-making groups and high-value commercial dealings.
• Demonstrated success working with large deals valued from $5M to $10M or more, strategic accounts, or significant implementation programs.
• Strong executive presence with the capacity to engage confidently with C-level executives, VP-level operators, technical contacts, and field staff.
• Experience leading complex, multi-stakeholder implementations requiring cross-functional coordination, change management, and operational excellence.
• Ability to handle both high-level strategic customer relationships and detailed tactical deployment aspects.
• Commercial acumen with experience identifying and fostering upsell, expansion, renewals, and overall account growth.
• Comfortable managing technical products integrating hardware, software, infrastructure, and logistics operations.
• Excellent communication skills including executive briefings, customer updates, issue escalation, and internal alignment.
• Ability to successfully navigate an early-stage environment, building playbooks while managing active workflows.
• Flexibility and willingness to travel up to 50% for customer meetings, deployment oversight, executive events, onsite implementation, and industry engagements.

Preferred Qualifications

• Background in sectors such as transportation, logistics, rail, supply chain, industrial automation, robotics, autonomy, hard tech, or enterprise infrastructure.
• Experience managing products that combine hardware deployment with complex software implementations.
• Direct involvement with operations or field teams in safety-critical or highly complex operational environments.
• Proven ability to build Customer Success or implementation functions from inception.
• Experience supporting customer expansions from initial deployments to broader commercial adoption.
• Experience with customer incentive plans, expansion targets, or account growth metrics.
• Exposure to representing the company at customer-facing events including executive forums, industry conferences, and strategic reviews.

Compensation

The annual salary for this role ranges from $180,000 to $200,000 USD, plus incentive compensation with on-target earnings expected between $250,000 and $300,000 USD. Compensation will align fairly with applicable laws and be based on experience, qualifications, skills, and location. Final salary will be determined during the hiring process.

Equal Opportunity Statement and Accessibility

Parallel Systems is an equal opportunity employer committed to fostering diversity and an inclusive workplace. All qualified candidates will receive consideration without regard to protected characteristics as per applicable laws. We are dedicated to creating an environment where everyone can excel. Reasonable accommodations for applicants with disabilities are available to ensure full participation, including during the application and interview processes. Candidates needing accommodations should contact their recruiter accordingly.