Candice McGrain

Chief of Staff to CEO

Pluralsight

Oct 2025 - Current (9 months)

Strategic Operations Manager, Office of CEO

Pluralsight

Dec 2024 - Oct 2025 (11 months)

Principal Program Manager

Pluralsight

Aug 2024 - Dec 2024 (5 months)

As a senior member of the EPMO Team, I led and managed large-scale, cross-functional programs, ensuring alignment with organizational priorities and delivering high-impact results on time and within budget. • Oversaw end-to-end program lifecycle, from inception through execution, including defining scope, aligning stakeholders, managing risks, and ensuring successful delivery of key milestones • Collaborated with senior leadership to define program objectives, set clear expectations, and ensure alignment across business units • Acted as a primary liaison between executive stakeholders and core project teams, providing transparent communication on progress, risks, and mitigation strategies • Facilitated regular program reviews with executiv

Program Management Consultant

Pluralsight

Oct 2023 - Aug 2024 (11 months)

Partnered with the SVP of Revenue Strategy and Operations to build a strong operational foundation, stand up project setting / tracking processes and run an effective organization • Established and led a consistent operating rhythm for the Revenue Services Organization Leadership Team - agenda setting, content creation and executing our RSO All Hands, Weekly Staff Meeting, Weekly GTM Leader Meetings, etc. • Maintained strong relationships with our RSO leaders and key stakeholders to drive progress and ensure a positive say/do ratio • Defined and executed our planning and tracking process to define our top RSO priorities - including OKR setting, tracking success metrics / progress, and cross functional alignment with IT, Marketing, Sales, a

Principal Program Management Leader, People Programs

Calendly

Aug 2022 - Sep 2023 (1 year 2 months)

Served as the Chief of Staff for our Chief HR Officer and team of 40+ HR professionals. Designed, led and executed our HR operating rhythm, annual / quarterly strategic planning processes, OKR setting, tracking + reporting cadence, project management office, and budgeting rhythm + reporting. • Established our HR operating rhythm and played an active role in the HR Leadership Team to ensure we were operating as a high performing organization • Defined, implemented and executed our HR operating rhythm - including content creation, training, communications and action & decision tracking • Defined and executed our HR OKR goal setting and KPI / health tracking processes • Managed our monthly OKR report out cadence and quarterly goal setting pr

Senior Program Management Leader, People Programs

Calendly

Aug 2021 - Aug 2022 (1 year 1 month)

Served as the Chief of Staff for our Chief HR Officer and team of 40+ HR professionals. Designed, led and executed our HR operating rhythm, annual / quarterly strategic planning processes, OKR setting, tracking + reporting cadence and project management office. • Established our HR operating rhythm and played an active role in the HR Leadership Team to ensure we were operating as a high performing organization • Defined, implemented and executed our HR operating rhythm - including content creation, training, communications and action & decision tracking • Defined and executed our HR OKR goal setting and KPI / health tracking processes • Managed our monthly OKR report out cadence and quarterly goal setting process • Created and designed ex

Director of Performance Management

AmplifiedAg

Mar 2021 - Aug 2021 (6 months)

Owned the creation, implementation and delivery of performance management rhythm and reporting. Also, lead all HR functionalities while HR Manager was on maternity leave. • Created and implemented a company-wide FMLA and Exit Interview process • Researched, designed and implemented innovative processes and procedures that will foster improvement • Aligned with HR to integrate performance management programs into the onboarding process for new associates and annual performance review process • Worked closely with HR to identify training needs and areas for improvement • Reviewed, monitored and analyzed performance results system wide and reports them accordingly • Developed and delivered communications regarding the strategic vision, sco

Strategic Program Manager, Office of CEO

Benefitfocus

Feb 2020 - Mar 2021 (1 year 2 months)

Led executive strategic initiatives + programs such as annual customer conference keynote, company re-brand and more. • Tracking and program management of strategic initiatives programs for Office of CEO, and other ad hoc project work • Lead strategic programs for the Office of CEO • Responsible for creating and executing on project plan for annual One Place user conference keynote • Developed effective processes and programs to drive key initiatives forward for the Executive Leadership Team • Defined project timelines, key milestones and deliverables while ensuring each project is driving forward • Led Corporate Website Rebrand initiative from scope to execution • Created status report process to ensure key blockers and risks have identif

Executive Assistant, President & CEO

Benefitfocus

Aug 2018 - Feb 2020 (1 year 7 months)

Supported the Office of the CEO in an administrative and project support capacity. Administration: • Managed calendar, travel, meetings and daily correspondence for the President and CEO • Lead the preparation, set up and break down of all executive internal and external customer meetings for the President and CEO, including by not limited to: meeting coordination, video conference set up, issue resolution, meals, agendas, guest travel, minutes and action follow ups • Responsible for expense report submissions, and approvals of leadership expense reports • Managed and organizes inbox for the President and CEO Project: • Defined new process for document management for Executive Leadership Team using Microsoft Teams, Sharepoint and One Dri

Business Operations II, Account Services

Benefitfocus

Nov 2017 - Aug 2018 (10 months)

Owned the creation of new processes & operational strategies, workforce & capacity planning, financial revenue reporting & auditing, and training content creation & delivery. • Created meeting agenda, outcomes and presentations for various internal and external meetings • Met frequently with internal leaders and teams for actions and progress on internal and external projects • Partnered with the Program Manager and Business Process Manager on the creation, planning and execution for new processes and documentation • Audited and created sales pipeline reports, and partnered with the Account Services Finance Director to build weekly financial reports in excel • Set colors and logos for branding of portal home page for Consumer Directed Hea

Executive Assistant

Benefitfocus

Sep 2015 - Aug 2018 (3 years)

Performed an extensive array of administrative tasks for the SVP of Account Services (former SVP, Engineering). This included managing complicated internal/external meeting schedules, domestic and international travel logistics, sales analysis reporting, and content creation for internal, external, and board meetings while maintaining confidentiality of all work material • Prepared and revised correspondence on behalf of the SVP • Took minutes for applicable meetings and drove follow up on action items • Supported the entire Engineering Leadership team consisting of the SVP, 5 VPs and 3 Sr. Directors • Planned and organized all travel and itineraries for leaders in my organization • Planned and organized agendas, logistics and travel for c

Technical Recruiter

Benefitfocus

Apr 2013 - Sep 2015 (2 years 6 months)

Responsible for full life cycle recruiting; job description creation, partnering with hiring managers, sourcing, interviewing, offer approval discussions with executive leadership team, candidate offer negotiation, background checks, completed offer paperwork and assisted with onboarding process • Supported all hiring needs for Implementation, Product, Finance, Technology and Engineering, while also supporting Operations and Sales hiring as needed • Eliminated the use of third party agencies for all Engineering and Technology hiring needs while maintaining a strong relationship with our preferred vendors • Partnered with Operations Recruiter and successfully doubled our expected annual hiring goals • Coached new hiring managers on job desc

Recruiter

Talon Professional Services

Jul 2011 - Apr 2013 (1 year 10 months)

Managed the entire recruitment lifecycle, from pre-screening to offer negotiations, across business units in information technology and engineering Positions recruited for: Help Desk, Systems Administrators, Infrastructure Engineers, Software Developers, Web Developers, Network Engineers, Linux/Unix Engineers, Application Development Managers, Infrastructure Managers, Principle Research Engineers, Mobile Developer, Data Analysts, Product Managers and Project Managers

W

Game Night Promotions Intern

Wachovia Spectrum

Sep 2009 - Jan 2010 (5 months)

C

Sales Intern

Comcast Spectacor Wachovia Spectrum

Aug 2009 - Jan 2010 (6 months)

U

Intramural Supervisor

University Intramurals

Sep 2007 - May 2011 (3 years 9 months)

D

Marketing/Advertising Temp

Discovery Semiconductors

Sep 2008 - Dec 2010 (2 years 4 months)

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