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Jobs at RedSail Technologies (Now Hiring) — 5 open

RedSail Technologies logoRedSail Technologies

Sr Director, People Operations & Total Rewards

Oak Brook, Illinois, United States · Hybrid

$160k–$180k/yr

Senior+

Sr. Director, People Operations & Total Rewards Job Summary The Sr. Director, People Operations & Total Rewards is a senior HR leader responsible for designing and leading RedSail’s compensation, benefits, and HR o…

Skills: Compensation Design, Benefits Strategy, HR Operations, Executive Presence, Vendor Management

RedSail Technologies logoRedSail Technologies

Product Designer

Oak Brook, Illinois, United States · Hybrid

$100k–$150k/yr

Senior

Product Designer Job Summary We’re looking for a Product Designer to help shape and execute the product experience for RedSail RxMarket. This role will focus on designing intuitive, high-impact workflows across our…

Skills: UI Design, UX Design, Product Design, User Research, Usability Testing

RedSail Technologies logoRedSail Technologies

Onboarding Coordinator

Shreveport, Louisiana, United States · Remote OK

$22/hr–$25/hr

Entry level

Job Summary The Onboarding Coordinator is responsible for overseeing and coordinating the scheduling, planning, and execution of installation projects. Acting as a liaison between customers, installers, and internal depa…

Skills: Project Coordination, Scheduling, Customer Service, Multitasking, Interpersonal Communication

RedSail Technologies logoRedSail Technologies

Software Development Engineer III

Oak Brook, Illinois, United States · Remote OK

$100k–$150k/yr

Senior

Software Development Eng. III Job Summary The Software Development Engineer III will be involved in the design and implementation of products that exceed functional expectations consistent with the values of RedSail Tech…

Skills: C#, .NET Framework, Angular, PostgresDB, MongoDB

RedSail Technologies logoRedSail Technologies

Installer

Grapevine, Texas, United States · Hybrid

$21/hr–$23/hr

Entry level

Job Summary The Installer position installs hardware primarily in retail pharmacy environments and trains the pharmacy staff on how to use the PioneerRX (PRx) software. This position requires extensive, nationwide travel…

Skills: Hardware Installation, Software Training, IT Networking, Windows OS, Troubleshooting

RedSail Technologies logo

Sr Director, People Operations & Total Rewards

RedSail Technologies

Oak Brook, Illinois, United States • Hybrid

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Senior+

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  • $160k–$180k/yr
  • Full-time
  • bachelor degree, postgraduate degree, professional certificate
  • Paid Time Off, 401k Match, Bonus Opportunities, Medical Insurance, Dental Insurance, Vision Insurance
  • Posted 5d ago
  • ~40 hrs/week

Responsibilities

Lead the design and execution of RedSail's total rewards strategy, including compensation, benefits, and HR operations infrastructure. Serve as a senior HR Business Partner to executive leadership while managing a team of People Operations professionals.

Requirements

Requires a bachelor's degree and over ten years of progressive HR experience, with at least five years in a senior leadership role. Expertise in compensation design, benefits strategy, and HRIS management is essential.

Full job description

Sr. Director, People Operations & Total Rewards

 

Job Summary

 

The Sr. Director, People Operations & Total Rewards is a senior HR leader responsible for designing and leading RedSail’s compensation, benefits, and HR operations strategy. This role sits at the intersection of total rewards strategy, HR operations excellence, and business partnership, ensuring RedSail has the scalable people infrastructure, competitive rewards programs, and leadership advisory support needed to enable growth. Reporting to the Chief People Officer, this leader ensures RedSail's pay and benefits programs are competitive, equitable, and sustainable, while building scalable HR operations infrastructure that supports a growing organization. The Sr. Director also serves as an HR Business Partner to assigned senior leaders and functions, develops HR talent, and partners closely with Finance, Payroll, Legal, and senior HR leadership to align total rewards strategy with business objectives. This individual also serves as a trusted advisor to the CPO and executive team.

 

Key Duties

 

Total Rewards

  • Own the enterprise compensation strategy, including salary structures, job leveling, and incentive programs that ensure internal equity and market competitiveness.
  • Lead annual compensation planning cycles and ongoing market benchmarking and pay equity analysis, partnering with Finance and business leaders to keep pay practices competitive, defensible, and compliant.
  • Own the design, vendor management, and cost strategy for health & welfare and retirement (401(k)) benefits programs, including annual open enrollment.
  • Evaluate benefits plan performance, cost trends, and utilization, recommending plan design changes that balance employee experience with cost management.

People Operations and Compliance

  • Own the People Operations function, including HRIS strategy, payroll partnership, HR compliance and data integrity across the employee lifecycle.
  • Identify and lead HR technology, workflow, and process improvements that increase efficiency, strengthen data quality, and improve the employee and leader experience.
  • Establish and maintain HR operations and total rewards metrics, dashboards, and reporting routines that provide visibility into service levels, compliance, cost trends, employee experience, and program effectiveness.

HR Business Partnership

  • Serve as the HR Business Partner to assigned senior leaders and functions, providing proactive counsel on organizational design, workforce planning, and complex employee relations matters.
  • Advise business leaders on compensation structuring for new roles, promotions, and organizational changes, ensuring decisions align with both business needs and total rewards strategy.
  • Represent the human capital perspective in business planning discussions, serving as a bridge between business strategy and HR program delivery.

Team Leadership & HR Talent Development

  • Lead, develop, and inspire a team of People Operations and Total Rewards professionals, building a high-performing, service-oriented team culture.
  • Build team capability and future HR leadership bench strength through individual development plans, stretch assignments, mentorship, and clear performance expectations.
  • Lead change management and communication planning for total rewards, HR operations, HR technology, and compliance initiatives to drive adoption, minimize disruption, and ensure leaders and employees understand what is changing and why.
  • Serve as a senior thought leader across the HR pillar, contributing to enterprise HR strategy alongside the CPO and peer HR leaders.
  • Ensure programs and practices are equitable, legally compliant, and aligned with RedSail's values and policies.
  • Support HR diligence and integration activities for acquisitions.
  • Performs other duties as assigned.

Education/Training

  • Bachelor's degree in Human Resources, Business, Finance, or a related field required; Master's degree or relevant certification, such as CCP, CEBS, or SHRM-SCP, preferred.
  • Ten or more years of progressive HR experience, including significant depth in compensation, benefits, or HR operations, with at least five years in a senior leadership role managing teams and programs at an enterprise level.

Required Work Experience/Skills

  • Demonstrated expertise in compensation design, benefits strategy, and HR operations, with a track record of building programs that are competitive, compliant, and scalable.
  • Executive presence and the ability to build credibility with and influence senior leaders, including C-suite stakeholders.
  • Experience partnering with Payroll, Finance, and Legal on complex compensation, benefits, and compliance matters.
  • Proven ability to lead, develop, and inspire high-performing teams in a fast-paced, growth-oriented environment.
  • Strong vendor management skills, with experience negotiating and managing broker, carrier, and HRIS vendor relationships.
  • Demonstrated ability to lead cross-functional process improvements that simplify workflows, increase operational efficiency, and improve stakeholder experience.
  • Excellent communication and consultative skills, with the ability to explain complex concepts clearly to employees and leaders at all levels.
  • Strong proficiency with HRIS platforms, compensation management tools, and Microsoft Office applications.

Discretionary Judgment

  • Regularly exercises high-level independent judgment on sensitive, complex, and confidential matters involving compensation, benefits, and HR compliance.
  • Uses good judgment and possesses ethical work values; models integrity and discretion in all aspects of the role.
 

Physical Demands, Working Conditions, and General Employment Guidelines

  • Moderate or high levels of stress may be experienced in the performance of the job
  • Position is performed in a general office environment, home office, or approved remote workspace where physical work includes, but is not limited to, sitting, standing, reaching, kneeling, bending, and lifting to 25 lbs.

Equipment

  • Must have high speed internet access and suitable home office setup in order to work a hybrid schedule.

Safety to Self and Others

  • Little responsibility for safety of others. Job is performed in an office setting where there are no hazardous materials or equipment.

Working Conditions/Hazards

  • Position is performed in an open office environment or approved remote work location.

Salary Range

  •  $160,000 - $180,000 

 

Work Location

  • Near any RedSail office.

 

Benefits Include: PTO, 401k (5%) Match, Bonus Opportunities, Medical/Dental/Vision Insurance, Work-life balance, Health Clinic, Fitness Bonus and Professional Development.

Related keywords

Total RewardsCompensation StrategyBenefits AdministrationHRIS401(k)CCPCEBSSHRM-SCPJob LevelingPay EquityHR ComplianceWorkforce PlanningOrganizational DesignVendor ManagementPeople OperationsHuman Capital

About RedSail Technologies

LinkedInVisit site
Industry
Software Development
Company size
501-1,000 employees
Headquarters
Spartanburg, South Carolina
LinkedIn followers
11,470

RedSail Technologies, LLC, is empowering pharmacy and transforming care with a network of over 11,500+ pharmacies serving more than 8 million patients monthly. RedSail has deep experience across sectors – community, long-term care, outpatient, clinic, HME/DME, and specialty pharmacies – and their pharma, payer, and strategic industry partners. PioneerRx® is RedSail’s industry-leading pharmacy management system for independent/retail pharmacy. Axys® is our modern software for long-term care and institutional pharmacy. PowerLine® provides scalable, HIPAA-compliant pharmacy transaction and data services, and QS/1® remains a trusted, comprehensive pharmacy management system. PioneerRx, QS/1, and PowerLine have earned HITRUST Risk-based, 2-year (r2) Certification status for information security, showcasing our strong commitment to protecting our customers' sensitive data and meeting/exceeding compliance regulations. 600+ RedSail employees support customers throughout the United States, providing the solutions that liberate them to focus on patients.

Offices: 201 W. Saint John Street, Spartanburg, South Carolina 29306, US · 600 Las Colinas Blvd E, Ste 2200, Irving, Texas 75039, US · 408 Kay Ln, Shreveport, Louisiana 71115, US

Information TechnologyHealth CareSoftware
View all jobs at RedSail Technologies

About RedSail Technologies

LinkedInVisit site
Industry
Software Development
Company size
501-1,000 employees
Headquarters
Spartanburg, South Carolina
LinkedIn followers
11,470

RedSail Technologies, LLC, is empowering pharmacy and transforming care with a network of over 11,500+ pharmacies serving more than 8 million patients monthly. RedSail has deep experience across sectors – community, long-term care, outpatient, clinic, HME/DME, and specialty pharmacies – and their pharma, payer, and strategic industry partners. PioneerRx® is RedSail’s industry-leading pharmacy management system for independent/retail pharmacy. Axys® is our modern software for long-term care and institutional pharmacy. PowerLine® provides scalable, HIPAA-compliant pharmacy transaction and data services, and QS/1® remains a trusted, comprehensive pharmacy management system. PioneerRx, QS/1, and PowerLine have earned HITRUST Risk-based, 2-year (r2) Certification status for information security, showcasing our strong commitment to protecting our customers' sensitive data and meeting/exceeding compliance regulations. 600+ RedSail employees support customers throughout the United States, providing the solutions that liberate them to focus on patients.

Offices: 201 W. Saint John Street, Spartanburg, South Carolina 29306, US · 600 Las Colinas Blvd E, Ste 2200, Irving, Texas 75039, US · 408 Kay Ln, Shreveport, Louisiana 71115, US

Information TechnologyHealth CareSoftware
View all jobs at RedSail Technologies

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