Remote Chief Operating Officer Insurance Jobs in Indiana

This is a remote role.

About Us
Reachdesk is the first truly end-to-end global SaaS gifting and swag platform, helping B2B companies create meaningful connections with prospects, customers, and employees, while driving measurable ROI.
We believe gifting is more than just a transaction: it's about building genuine human connections that fuel business growth. Whether you're engaging prospects, celebrating customers, or recognizing employees, our platform makes it easy to deliver personalized gifts, branded swag, and unforgettable event & brand experiences at scale through automated sourcing, storage, and global delivery.
We're growing, and we're currently looking for a Head of Business Systems & Operations to join us.

The Role

As the Head of Business Systems & Operations at Reachdesk, you will own and shape the systems and data architecture that underpin how the business operates. You will be responsible for connecting Finance, GTM, Product, and Customer teams through a single, trusted system landscape, ensuring data flows cleanly across Salesforce, NetSuite, Workato, and our BI layer. This is a high impact role where you will define how the business uses its systems, not just maintain them.

You will join at a critical stage as we complete our closed-loop architecture and transition ownership from product into the business. You will have full autonomy to design, govern, and evolve this ecosystem while embedding AI into core workflows and decision making. This role is particularly suited to someone who enjoys creating order from complexity: building a reliable, scalable foundation that the business trusts, enabling faster decisions, stronger financial control, and a step change in operational efficiency across Reachdesk.

Your Responsibilities

• Own the end-to-end systems and data architecture connecting Salesforce, NetSuite, Workato, the Reachdesk SaaS platform and the BI layer.
• Lead the transition of systems ownership into Business Operations and establish a clear operating model, governance framework, and roadmap that the business trusts and that can evolve as needs change, ensuring trusted, timely data flows across Finance, GTM, Product, and Customer teams.
• Lead from the front by setting technical direction from being in the systems alongside your team, not just reviewing their work. Define the go-forward BI architecture, ownership model, and roadmap.. 
• Complete and continuously evolve this architecture so every core process is underpinned by clean data and reliable automation.
• Establish an AI governance framework to embed AI into core workflows and decision-making, from forecasting and pipeline insights to customer health, billing, and operational automation, delivering measurable efficiency gains.
• Define and enforce master data management and integration standards across all systems.
• Partner closely with Finance, RevOps, Customer Operations, and Product to translate business priorities into scalable system solutions, balancing speed of delivery with long-term architectural integrity.
• Build, lead, and develop a small, high-performing team of systems and operations specialists, and manage external delivery partners where needed.
• Own vendor relationships, contracts, and roadmaps for our core SaaS stack, ensuring we get value, leverage, and influence over product direction, with a focus on finding efficiencies and cost savings.  
• Define and report on system health, data quality, and operational efficiency KPIs to the executive team and Board where relevant.

About You

You are a strategic systems leader with strong technical instincts and a pragmatic builder mentality. You see business systems as a competitive advantage, not a back-office function, and you are energized by the opportunity to shape the operating engine of a high-growth, PE-backed SaaS business. You understand the importance and value of data integrity and consistency, ensuring every department relies on the same core data and metrics. You are still in the system. You are as comfortable in a Salesforce flow, a NetSuite saved search, or a Workato recipe as you are in a strategy meeting. You believe leaders in this function lose their edge the moment they stop building, and you have no interest in becoming that person. You move comfortably between architecture decisions and detailed configuration, and you are equally at home in a conversation with the CFO, the CRO, or an engineer. You bring a hands-on operator mindset: you understand that great systems exist to make the business faster, sharper, and more accountable, and you measure your success by the decisions and outcomes they enable.

Must-have Qualifications

• 8+ years in Business Systems, RevOps, or BizTech leadership roles within B2B SaaS, with at least 3 years leading a function or team.
• Deep expertise across Salesforce and NetSuite, including a track record of designing and evolving the integration layer between them.
• Strong experience with iPaaS platforms (Workato strongly preferred) and modern BI tooling.
• Demonstrated ability to design and operate a closed-loop architecture, covering quote-to-cash, lead-to-revenue, and customer lifecycle, in a multi-entity, multi-currency environment.
• Demonstrably hands-on within the last 12 months and can speak in concrete detail about systems you have personally configured, automations you have built, or data models you have designed.
• Robust data governance and master data management discipline, with a clear point of view on ownership, lineage, and quality.
• Proven track record of leading complex, cross-functional systems programs end-to-end, on time and on budget.
• Excellent stakeholder management, particularly with Finance and GTM leadership, and the ability to translate technical decisions into commercial impact.
• People leadership experience with a coaching mindset, and the ability to build a small team that punches above its weight.

Preferred Qualifications

• Experience in a PE-backed, high-growth SaaS environment with tight financial control requirements.
• Familiarity with multi-stream revenue models (e.g. SaaS combined with services, marketplace, or fulfillment) and the revenue recognition complexity they bring.
• Experience embedding AI/ML or agentic automation into operational workflows, with named use cases, governance, adoption controls, and measurable business outcomes.
• NetSuite and/or Salesforce certifications.
• Experience transitioning systems ownership into a Business Operations function.
• Background working in a scaling SaaS business, comfortable operating across time zones and entities.

The Benefits

• Competitive salary with generous stock options
• 401(k) with employer match
• Medical, dental & vision insurance, including mental health support and fast access to care
• Flexible PTO that increases the longer you're with us, plus extra flexibility for life's unexpected moments
• A genuinely collaborative culture with innovative, fun, and ambitious people

Reachdesk believes that a diverse team helps us achieve our mission faster, and so we welcome applicants from all backgrounds. Compensation is based on standardised salary ranges by role, level, and location, benchmarked against similar-sized companies. Final offers are determined by a combination of experience, skills, and role fit, and may vary from the listed range.

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