Headway

Staff Software Engineer - Experimentation

Headway
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2 months ago
Remote, United States +3 moreStaff+
H1B sponsor

Base Salary

$265k - $331k/yr

Responsibilities

  • Own and evolve Headway’s experimentation and feature-flagging platform, including assignment, exposure, identity resolution, and experiment data pipelines.
  • Evaluate and consolidate LaunchDarkly and Statsig and make build-versus-buy and warehouse-native architecture decisions.
  • Build market-based experimentation capabilities for a multi-sided marketplace, including geographic testing and long-term holdout groups.
  • Develop AI-assisted experiment validation and automated detection of broken experiments.
  • Raise company-wide experimentation quality through defaults, templates, reviews, documentation, education, and migrations.
  • Gather requirements across teams, sequence a roadmap, provide technical product direction, and mentor senior engineers.
  • Partner with Data Science on statistical validity and with event-tracking and metric-definition owners on measurement quality.
  • Work across backend services, frontend rendering, CDN behavior, and the data warehouse.

Requirements

  • Staff-level software engineering experience with end-to-end ownership of an experimentation or feature-flagging stack.
  • Experience building experimentation primitives such as persistent assignment, accurate exposure tracking, cross-session and cross-device identity resolution, or experiment diagnostics.
  • Fluency in experimentation statistics and ability to partner effectively with data scientists on measurement validity.
  • Experience debugging uneven traffic splits, cross-arm user assignment, exposure discrepancies, and broken identity resolution.
  • Experience building an organizational experimentation program through defaults, templates, review, teaching, and documentation.
  • Experience making platform build-versus-buy decisions, evaluating vendor risk, and comparing hosted with warehouse-native approaches.
  • Experience landing migrations with teams that did not initially request them.
  • Ability to use AI effectively while recognizing situations requiring human judgment.
  • Experience driving technical direction through design documents, reviews, and planning cycles and mentoring senior engineers.
  • Willingness to work across backend, frontend, CDN, and data warehouse systems.
  • Experience with multi-sided marketplaces, growth or search and ranking systems, or healthcare is preferred but not required.

Benefits

  • Base pay range is $265,000-$331,000, with possible equity eligibility depending on position and level.
  • Equity compensation, medical, dental, and vision coverage, HSA/FSA, and 401(k).
  • Work-from-home stipend, therapy reimbursement, Carrot Fertility annual reimbursement and membership, and an Employee Assistance Program.
  • 16-week parental leave for eligible employees.
  • 16 paid holidays, including a holiday break between December 25 and December 31, plus flexible PTO.
  • Training and professional development opportunities.
  • Remote work support is provided through a work-from-home stipend.

Tech Stack

Apache KafkaApache SparkAWSCloudflareDatadogdbtFastAPIPostgreSQLPythonReactRedisSnowflakeTypeScript

Categories

Headway

About Headway

1,001-5,000 employees

Headway builds a software-enabled network that makes it easy for therapists to accept insurance and for patients to find in-network mental health care. Its platform handles credentialing, scheduling, claims, and payment reconciliation, matching patients to licensed providers and partnering with health plans to expand access. Founded in 2019 and headquartered in New York, the privately held company operates across the United States.

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