Director of Customer Success

The 1099 economy is the fastest-growing segment of the American workforce, and it's been running on duct tape and spreadsheets. A credentialing gap or an uninsured worker isn't just an HR headache here – it's a liability that can shut down a business.

GigSafe is a contractor management platform built for gig and last-mile delivery operations. We are building infrastructure for the future of 1099 work that helps companies pay independent contractors accurately, on time, and in compliance.

This is a big problem. A large market. And we're early. Come build with us.

For more information, visit gigsafe.com.

The Director of Customer Success owns the relationship between GigSafe and its customers, and is the person we're hiring to build the CS function from the ground up. This is a people leadership role, but it's not a hands-off one: you'll set the strategy, build the team, and serve as the senior escalation point when things get hard. You'll need to become a genuine expert in GigSafe's product and in 1099 compliance, because your team will look to you when they don't have the answer.

Our product is not perfect: we're a startup and we're honest about that. But the customer experience needs to be. That's why this role exists. You'll bridge the gap between where the product is today and the experience customers deserve, using your expertise, your team, and your relationships with Product to close that gap over time.

This role involves domestic travel. It won't always be frequent, and it won't always be glamorous, but when customers need a senior face in the room, that's you. Flexibility and willingness to show up in person is a requirement of the job.

• Own the overall health, retention, and growth of the customer portfolio, setting and tracking the KPIs that define what good looks like for the CS function

• Serve as executive sponsor for strategic and at-risk accounts, engaging directly with senior stakeholders

• Lead Quarterly Business Reviews and other high-stakes customer touchpoints

• Drive renewal and expansion outcomes in partnership with Sales, with direct accountability for net revenue retention

• Serve as the senior escalation point for the CS team: the person with the deepest product knowledge and compliance expertise in the room, so the team always has somewhere to go when an issue is beyond their scope

• Build the CS team from the ground up: define the structure, hire the right people, and create the environment where Account Managers can do their best work. You're not inheriting a finished team, you're building one

• Hire, onboard, and retain CS talent as the team scales

• Coach Account Managers on relationship strategy, escalation handling, product knowledge, and 1099 compliance, ensuring the whole team grows in expertise alongside the product

• Translate customer patterns into actionable input for Product, Operations, and Compliance: surfacing recurring issues, advocating for fixes, and closing the loop so customers see their feedback reflected in how the product evolves

• Build the CS strategy and operating model in partnership with the VP of Operations: defining how the function runs, what it measures, and how it scales as GigSafe grows

• Partner closely with Product to close the feedback loop between what customers experience and what gets built. Our product is evolving rapidly, and your input shapes that roadmap in a real and direct way

• Collaborate with Compliance and Business Ops where customer-facing obligations intersect with internal policy

• Report regularly to the VP of Operations on portfolio health, team performance, and strategic risks

• 8+ years in Customer Success, Account Management, or a related client-facing role

• 3+ years leading customer-facing teams, with experience building a CS function rather than just managing one – you know what it takes to stand something up from scratch

• Proven track record owning net revenue retention and driving expansion within an existing customer base

• Strong executive presence, with experience engaging senior stakeholders at customer organizations

• Comfortable with domestic travel – frequency will vary, but it's a real part of the role

• Willing and able to become a deep expert in GigSafe’s product and in 1099 compliance — your team will look to you for the answer when the situation is beyond them, and you need to have it.

• Experience in a startup or high-growth environment

• Experience in B2B, SaaS, logistics, or marketplace environments

• Comfort with 1099 compliance or workforce management

• Net revenue retention improves within the first year through a combination of reduced churn and expanded accounts

• Account Managers have clear portfolios, development plans, and are hitting their targets

• The Director is the go-to expert on GigSafe's product and 1099 compliance, internally and externally: trusted by the team, respected by customers, and credible with Product when advocating for change

• Customers feel well-served and supported, even when the product isn't perfect, because the team is responsive, knowledgeable, and proactive. The customer experience reflects the standard GigSafe is building toward, not just where the product is today

• Startup Mentality You're energized by ambiguity, not slowed down by it. When the playbook doesn't exist, you write it. You move fast, stay adaptable, and don't need perfect conditions to make progress.

• Give a Sh*t You care about the work, customers, contractors on the platform, and the people sitting next to you. You hold yourself to a high standard not because someone's watching, but because mediocrity bothers you.

• Ownership You treat the company's success as your own, because it is. You take responsibility for outcomes and you close the loop without being asked. When something's broken, you fix it – even if it's not your job.

• Collaborative You make the people around you better. Low ego, high trust, and emotionally intelligent. You communicate directly, share credit generously, and don't create unnecessary friction for your teammates.

• Critical Thinker You connect dots, figure things out, and bring solutions – not just problems. You're resourceful and intellectually curious, and you don't need hand-holding to do great work.

• Health, Dental & Vision: Comprehensive medical, dental, and vision coverage for employees and dependents

• Unlimited PTO: Flexible time off plus paid company holidays

• Competitive Compensation: Competitive base salary with opportunities for performance-based bonuses

• 401(k): Retirement savings plan

• Equity: Stock options giving employees a meaningful stake in GigSafe's growth

• Parental Leave: Paid leave for all new parents

GigSafe is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, national origin, age, disability, veteran status, sexual orientation, gender identity, or any other characteristic protected by applicable law.