• Skip to primary navigation
  • Skip to main content
  • Skip to footer

Side Hustles

Side Hustles

Side Hustles For All

  • Best Side Hustles
    • Woman sitting on a pile of coins and working on a laptop surrounded by icons representing different side hustle ideas

      31 Best Side Hustles to Earn Extra Money in 2026

    • Bicycle courier delivering food for their side hustle.

      What Is a Side Hustle?

    • Remote worker sitting at his desk making money from home

      18 Ways to Make Money from Home (Online and Offline Jobs)

    • By Category
      • Arts & Crafts
      • Business Services
      • Caregiving
      • Creative Services
      • Digital Freelance Services
      • View All
    • By Lifestyle
      • I’m introverted
      • I’m a man
      • I’m a woman
      • I’m a stay-at-home mom
      • I’m unique
      • View All
    • By Profession
      • Artists & Creatives
      • Musicians
      • Nurses
      • Physicians
      • Teachers
      • View All
    • By Age Group
      • College Students
      • Teens
      • Age 50+
      • Seniors
      • View All
    • By Skills & Interests
      • Get Paid to Lose Weight
      • Get Paid to Play Games
      • Get Paid to Read
      • Get Paid to Sleep
      • Get Paid to Travel
      • View All
  • Best Gig Apps
    • Freelance worker popping out of a phone screen and considering gig apps on the App Store and Google Play

      Top 6 Gig Apps to Make Real Cash in 2026

    • Smartphone surrounded by the icons of different money-making apps

      Top 10 Best Money-Making Apps to Try in 2026

    • two teenagers using job apps on a phone and laptop

      19 Job Apps for Teens to Find Jobs and Make Money

    • By Gig Type
      • Cashback
      • Data Entry
      • Delivery
      • Games
      • Product Testing
      • View All
    • By Payment Method
      • Bingo Games that Pay to Cash App
      • Games that Pay Real Money
      • Games that Pay to Cash App
      • Games that Pay via PayPal
      • Surveys that Pay to Cash App
      • View All
    • By Benefits
      • $20 Signup Bonuses
      • $25 Signup Bonuses
      • $50 Signup Bonuses
      • Best Signup Bonuses
      • Instant Signup Bonuses
      • View All
    • By Skills & Interests
      • Driving
      • Losing Weight
      • Playing Games
      • Product Testing
      • Watching Ads
      • View All
  • Job Hunting
    • Freelance worker browsing a job post on a freelance job board.

      23 Job Boards You Can Use to Find Remote Work

    • Freelance writer sitting at her laptop working on a project

      15 Best Remote Jobs That Require No Paid Work Experience

    • Teenager sitting at laptop working an online job

      14 Online Jobs for Teens (With No Experience)

    • Freelancing
      • Freelance Writing Sites
      • Freelance Writing Job Boards
      • Freelance Writing Platforms
      • View More
    • Gig & Shift Work
      • Gig Work Apps
      • On-Demand Work Apps
      • Shift Work Apps
      • View More
    • GPT (Get Paid To)
      • Microtasking
      • Product Testing
      • Survey Taking
      • View More
    • Remote Working
      • Best Remote Job Boards
      • Top 15 Remote Jobs
      • View More
  • Job Board
    • Work Schedule
      • Part-Time Jobs
      • Per-Diem Jobs
      • Go Search
    • Work Environment
      • Hybrid Jobs
      • Remote Jobs
      • Go Search
    • Employment Type
      • Contractor Jobs
      • Internship Jobs
      • Temporary Jobs
      • Go Search
    • Job Title
      • Accounting Jobs
      • Data Entry Jobs
      • Nursing Jobs
      • Online Teaching Jobs
      • Software Engineer Jobs
      • Go Search
    • State
      • California Jobs
      • Florida Jobs
      • New York Jobs
      • Pennsylvania Jobs
      • Texas Jobs
      • Go Search
    • City
      • Chicago, IL
      • Houston, TX
      • Los Angeles, CA
      • New York City, NY
      • Phoenix, AZ
      • Go Search

Home Flexible Job Board Head of Revenue Operations

$175,000–200,000/yr 37d ago

Head of Revenue Operations

Boost your chances before you apply.

  • ✨ Apply 10x Faster Free

    It takes 30+ tailored applications to land jobs like this one. We'll help you get that done in 1 hour.

    No Credit Card Required

  • Proceed to Application Go directly to the company's job page to apply.
Logo

Arcadia

US

Full-time Permanent Remote

✨ Apply 10x Faster

Analyze your resume for missing keywords, then one-click optimize it. Don't be anything less than a 100% match candidate.

Free

No Credit Card Required

Summary

The Head of Revenue Operations will design and scale the revenue operating system, including CRM infrastructure, forecasting models, and AI-powered reporting tools. They will act as a cross-functional leader to align Sales, Marketing, Finance, and Customer Success teams toward predictable growth.

Job Description

Arcadia is dedicated to happier, healthier days for all. We believe that there is a better healthcare world — one powered by data. Our platform transforms complex, diverse data into a unified foundation for health, helping organizations deliver better care, boost revenue, and lower costs.

We're a team of fiercely driven individuals committed to making healthcare more sustainable — and we're looking for passionate people to help us get there.

For more information, visit arcadia.io.

Arcadia helps healthcare and life sciences organizations deliver measurable results. We unify fragmented data across the healthcare ecosystem so payers, providers, ACOs, and life sciences companies can make confident decisions grounded in trustworthy intelligence. Our platform supports more than 200 organizations and 40 million attributed lives across value-based care, risk adjustment, population health, and life sciences programs.  

Why This Role Is Important to Arcadia

Arcadia's commercial team depends on consistent process, clean pipeline data, and forecasts to help manage and grow the business. As a fast-growing company, we need to scale our infrastructure, systems and operating model to one that aligns to the pace of the growth. This role owns the systems, tools, and cadences that make pipeline reviews, forecasting, and reporting consistent and accurate across the entire commercial team.

Part of the initial mandate is understanding the current ecosystem of tools and technology that support commercial and revenue operations today, and making recommendations on the optimal tech stack for the function going forward — one that is AI native. This person will be the accountable owner of that stack and roadmap, partnering closely with Product and Tech to build the AI-native operating system rather than building it in isolation.

This person will run point on sales operations and the forecasting cadence, and will build the AI-powered operating layer (dashboards, briefings, and workflow tools) that gives the entire commercial organization — not just its leadership — real-time visibility and leverage.

This is role is for someone who is execution oriented. You'll work in the tools yourself — not just direct others to — while also setting the strategy, systems, and rigor that let Sales, Marketing, Customer Success, Legal, and Finance move as one aligned, predictable engine.

\n

What You'll Be Doing

  • Own the revenue operating system, designing and scaling the processes, metrics, and infrastructure that drive consistent, predictable performance across the business
  • Partner with Systems Engineering to drive end-to-end improvements and scalability in Salesforce, including structure, data hygiene, workflow automation, and adoption across the sales org
  • Evaluate the current ecosystem of tools and technology supporting commercial and revenue operations, and make recommendations on the optimal, AI-native tech stack for the function
  • Serve as the accountable owner of that tech stack and roadmap, partnering closely with Product and Tech to build the AI-native operating system rather than building it in isolation
  • Own pricing strategy, SKUs, and the end-to-end quote-to-cash process, ensuring pricing structures and deal execution are clean, consistent, and scalable
  • Own the forecasting cadence and develop robust, repeatable forecasting models (pipeline, bookings, ARR) that improve accuracy and predictability
  • Build the AI-powered operating layer — automated briefings, pipeline intelligence, meeting prep, and reporting dashboards — that gives the commercial organization real-time visibility
  • Establish and maintain a unified KPI framework, ensuring alignment on definitions, visibility, and accountability across the funnel
  • Act as connective tissue across live opportunities, coordinating Marketing, Finance, the RFP team, Value Enablement, and Sales Engineering so they're effectively leveraged
  • Partner with Sales, Marketing, Customer Success, and Finance leadership to align execution with company goals and financial plans
  • Analyze pipeline health, conversion rates, and sales efficiency to identify opportunities and drive improvements
  • Design and manage sales compensation and incentive plans that align with business objectives and drive desired behaviors across GTM teams

 

What Success Looks Like

In 3 months

  • Build a deep understanding of Arcadia's GTM model, revenue streams, and key SaaS metrics (ARR, NDR, GDR, pipeline coverage, win rates, sales cycle)
  • Assess current RevOps infrastructure, CRM configuration, reporting, and forecasting methodologies
  • Map the current ecosystem of tools and technology supporting commercial and revenue operations, and begin forming a point of view on the optimal, AI-native tech stack
  • Establish trust across Sales, Marketing, Customer Success, and Finance leadership

In 6 months

  • Own the CRM and forecasting cadence end-to-end, with a unified KPI framework giving clear visibility into pipeline health, revenue performance, and GTM efficiency
  • Ship the first version of the AI-powered operating layer (automated briefings, dashboards, and reporting tools) that reduces manual reporting burden for commercial leadership
  • Improve forecast accuracy through enhanced pipeline modeling and data-driven insights

In 12 months

  • Operate a scalable revenue operating system — process, CRM, forecasting, and AI tooling — that enables predictable growth and aligns planning across GTM and Finance
  • Deliver consistent, high-confidence forecasts and actionable insights that directly inform the executive team's decisions
  • Improve key performance metrics (e.g., pipeline coverage, conversion rates, sales productivity, retention) through data-driven optimizatio

What You'll BringThe Role, Done Before

  • You have held this exact role — Head/Director of Revenue Operations or equivalent — at a company of similar growth stage, and can point to what you built and owned.

Growth-Stage Fluency

  • Track record of operating at growth-stage speed and ambiguity — scrappy, resourceful, and comfortable building infrastructure from scratch rather than administering something already built. Candidates whose experience is exclusively at large, mature organizations without growth-stage exposure are not a fit for this seat.

Deep SaaS Metrics Expertise

  • Strong command of key SaaS metrics including ARR, NDR, GDR, CAC, LTV, pipeline coverage, and sales productivity, and how they connect to business performance.

Forecasting & Modeling Rigor

  • Proven ability to build and operationalize forecasting models (e.g., pipeline velocity, ARR forecasting) that improve accuracy and predictability.

CRM & Systems Ownership

  • Deep, hands-on experience owning a CRM (Salesforce or equivalent) and the broader GTM tech stack — configuration, data integrity, and workflow design, not just consumption of dashboards.

Pricing & Quote-to-Cash Experience

  • Hands-on experience owning pricing strategy, SKU structure, and the quote-to-cash process, ideally in a company that scaled or restructured its pricing model.

AI-Forward

  • Comfortable using AI tools to build operational leverage — automating reporting, briefings, and workflows rather than relying solely on headcount to scale.

Cross-Functional Leadership

  • Track record of partnering effectively with Sales, Marketing, Customer Success, Finance, and executive leadership to drive alignment and results.

Operator Mindset

  • Ability to move between strategy and execution, translating insights into action and driving measurable impact.

Would Love for You to Have

  • 8–12+ years of experience across Revenue Operations, Sales Operations, or GTM analytics in a SaaS environment
  • Experience supporting a high-growth SaaS company through key milestones (e.g., post-acquisition integration, scale-up, or M&A)
  • Familiarity with modern BI, AI, and planning tools (e.g., Sigma, Adaptive, Salesforce ecosystem, AI-native reporting/agent tools) and building self-service analytics environments
  • Experience designing and optimizing sales compensation plans at scale

What You'll Get

  • The mandate to build a consistent, predictable commercial engine — including its AI-powered tooling — rather than inherit and maintain one
  • A growth path from individual contributor to leading the people and functions that support sales operations as Arcadia scales
  • A mission-driven culture where your work supports better healthcare outcomes
  • Competitive compensation and strong benefits, including Flexible Time Off
  • A collaborative, data-driven environment focused on impact, ownership, and continuous improvement

\n$185,000 - $200,000 a yearThis role is bonus eligible\n

About Arcadia

Arcadia.io helps innovative providers and payers across the country transform healthcare to reduce cost while improving patient health. We do this by aggregating large amounts of disparate data, applying algorithms to identify opportunities to provide better patient care, and making those opportunities actionable by physicians at the point of care in near-real time. We are passionate about helping our customers drive meaningful outcomes. We are growing fast and have emerged as a market leader in the highly competitive population health management software market and have been recognized by industry analysts KLAS, IDC, Forrester, and Chilmark for our leadership. For a better sense of our brand and products, please explore our website.

Protect Yourself

If you have concerns about the authenticity of a job offer or recruitment-related communication claiming to be from Arcadia, we encourage you to verify by contacting us directly at (781) 202-3600 and select option 3. For more information, visit our website.

This position is responsible for following all Security policies and procedures in order to protect all PHI under Arcadia's custodianship as well as Arcadia Intellectual Properties.  For any security-specific roles, the responsibilities would be further defined by the hiring manager.

About the company

Arcadia

Arcadia® is the most trusted healthcare platform for outcomes, connecting and transforming complex healthcare data into trusted intelligence. We unify data across the healthcare ecosystem and convert that information into actionable analytics, AI-driven intelligence, and performance benchmarks. Arcadia helps organizations act with clarity to achieve clinical, operational, and financial outcomes that accelerate their impact across enterprises.

Built on a comprehensive data foundation spanning tens of millions of patient lives, Arcadia supports hundreds of organizations, including Aetna, Highmark Blue Cross Blue Shield, Ochsner Health, WakeMed Key Community Care, Merck, and the California Department of Health Care Services. We are a trusted provider paving the way in data-driven healthcare. Learn more at arcadia.io.

Founded

2007

Company size

201-500 employees

Industry

Software Development

Org type

Privately Held

Headquarters

Boston, Massachusetts

Apply Now

About the company

Arcadia

Arcadia® is the most trusted healthcare platform for outcomes, connecting and transforming complex healthcare data into trusted intelligence. We unify data across the healthcare ecosystem and convert that information into actionable analytics, AI-driven intelligence, and performance benchmarks. Arcadia helps organizations act with clarity to achieve clinical, operational, and financial outcomes that accelerate their impact across enterprises.

Built on a comprehensive data foundation spanning tens of millions of patient lives, Arcadia supports hundreds of organizations, including Aetna, Highmark Blue Cross Blue Shield, Ochsner Health, WakeMed Key Community Care, Merck, and the California Department of Health Care Services. We are a trusted provider paving the way in data-driven healthcare. Learn more at arcadia.io.

Founded

2007

Company size

201-500 employees

Industry

Software Development

Org type

Privately Held

Headquarters

Boston, Massachusetts

Footer

sidehustles.com
Facebook Twitter Instagram LinkedIn Reddit TikTok YouTube

Show Me The Money

  • Side Hustle Basics
  • Side Hustle Job Board (Remote & Part-Time Jobs)
  • Gig App Reviews
  • Job Hunting
  • Manage Your Money
  • The Gig Apple: News & Events

Company

  • About Us
  • Contact Us
  • Become a Contributor
  • Advertising & Sponsorships
  • Partner With Us
  • Editorial Guidelines

Side Hustles © All rights reserved

  • Privacy Policy
  • Terms of Service

Thanks for using our free job board

Your review would mean a lot to us.

If you love that we're just giving away remote jobs for free with no paywall, please spread the word. (You will need to create an account on Trustpilot, for which we'll be eternally grateful.) Good luck out there!

Leave a Review Not yet. Send me to the job post.