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Senior Manager, Agent Success

USA
H

Headway

Startup
Category
Ops
Experience
8+ years
Type
Full-Time
Location
USA
Salary
$130,560 - $192,000
Job Description
Benefits & Culture
Equity Compensation
Medical
Dental
Vision
401K
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Response Rate
85%
Avg Response Time
2 hours
Compensation Calculator
In startups, higher salary usually means lower equity.
Salary (affects equity %)
Link salary ↔ equity
$125,000
$130,560$192,000
Equity % (auto from trade-off model)
1.19%
0%5%
Projected Exit Value
$350,000,000
$10M$500M
Live Trade-off
Salary
Equity %
Est. Equity Value at Exit
$100,000
1.19%
$2,082,500
$125,000
1.19%
$2,082,500
$150,000
0.97%
$1,705,977
$175,000
0.70%
$1,221,764

Advanced Salary & Equity Calculator

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About the Role:

The Agent Success function ensures that our Customer Experience teams are consistently equipped, supported, and enabled to deliver an exceptional customer experience at every interaction.

We’re seeking a Senior Manager, Agent Success to lead and integrate our Enablement, Knowledge Management, and QA programs. You’ll manage an established team, bring strategic leadership, and build scalable operating systems to drive excellence across our frontline operations. This is a critical leadership role that will have a direct impact on customer satisfaction, operational efficiency, and the performance of hundreds of agents.

You Will:

  1. Lead the Enablement, Knowledge Management, and QA teams, ensuring strategic alignment and collaboration across pillars.
  2. Develop and execute a cohesive Agent Success strategy informed by QA insights and operational data.
  3. Build scalable, high-impact enablement programs for onboarding, ongoing training, and continuous skill development.
  4. Ensure our knowledge base is accurate, accessible, and integrated into workflows for maximum efficiency.
  5. Oversee quality assessment programs to monitor and improve agent performance across all support channels.
  6. Create feedback loops between QA, enablement, and knowledge to continuously improve processes and outcomes.
  7. Partner with cross-functional teams (WFM, Vendor Management, Product, Data) to support operational priorities and drive results

You’d be a great fit if:

  1. Have 7+ years in customer experience operations, enablement, or quality assurance leadership, ideally in high-scale environments.
  2. Are a proven people manager with a track record of developing high-performing teams.
  3. Are data-driven and skilled at translating performance metrics into actionable improvements.
  4. Have experience building scalable enablement and QA programs for internal and outsourced teams.
  5. Are highly organized, operationally excellent, and adept at leading in complex, fast-paced environments.
  6. Have strong collaboration and influencing skills with the ability to align multiple stakeholders.

Compensation and Benefits:

The expected base pay range for this position is $130560 - $192000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for performance-based variable compensation and an equity grant, depending on the position and level. We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Benefits offered include:

  1. Equity Compensation
  2. Medical, Dental, and Vision coverage
  3. HSA / FSA
  4. 401K
  5. Work-from-Home Stipend
  6. Therapy Reimbursement
  7. 16-week parental leave for eligible employees
  8. Carrot Fertility annual reimbursement and membership
  9. 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
  10. Flexible PTO
  11. Employee Assistance Program (EAP)
  12. Training and professional development