The Opportunity:
LegalShield (PPLSI) is a pioneering provider of subscription-based legal and identity theft protection plans to individuals, families, and businesses in North America. Operating through two brands — LegalShield and IDShield — the company serves 1.8 million active members through a network of nearly 40 law firms across the US and Canada. Founded in 1972, LegalShield is dedicated to the belief that everyone deserves a secure life and equal treatment under the law. Backed by Stone Point Capital, the company is investing in growth, technology modernization, and operational excellence.
We are seeking a Director of Tax to own the full tax function for a complex, multi-entity, multi-jurisdiction organization. This role encompasses federal and state income tax, international tax (Canada), indirect taxes (sales, gross receipts, premium, property), payroll tax compliance, tax provision, and tax planning. Reporting directly to the CFO, you will be the company’s senior tax authority — setting tax strategy, managing external compliance advisors, leading audits, calculating provisions, and ensuring every filing is accurate and timely.
The current operating model relies on external advisors for the majority of compliance preparation, with the Director providing internal oversight, provision work, estimated payments, and strategic judgment. You will be expected to evaluate this model with fresh eyes — optimizing the balance between internal execution and external advisory, managing advisor spend for value, and ensuring the company has the right tax infrastructure for its growth trajectory. This is a hands-on leadership role in a PE-backed environment where precision, speed, and proactive planning are expected.
The Scope:
The Director of Tax is the single point of accountability for all tax compliance, provision, and planning activities across the PPLSI family of entities. The role covers a broad tax surface: a consolidated federal return, a Canadian federal return, multi-state income and franchise taxes, premium taxes (insurance-regulated entities), sales and use taxes, gross receipts and B&O taxes, property taxes, payroll taxes, and various local jurisdiction filings.
The company’s external tax advisors currently handle the majority of return preparation and compliance filing (~$130K annual spend), focused exclusively on compliance. The Director owns the provision, estimated tax payments, and all tax planning internally. The Director will manage the external advisor relationship end-to-end — scoping engagements, negotiating fees, setting quality and timeline expectations, reviewing deliverables, and continuously evaluating whether the current in-house vs. outsourced mix is optimal.
The Director will manage one direct report (Tax Analyst) and work closely with the Controller on matters that intersect financial reporting — including deferred tax assets/liabilities, book-to-tax differences on intangible assets and equity compensation, and statutory basis reporting for regulated entities. As a direct report to the CFO, the Director will also be expected to contribute to strategic tax planning for M&A, entity structuring, and sponsor-level reporting.Responsibilities:
Performance Outcomes
External Advisor & Vendor Management
Own the end-to-end relationship with external tax compliance advisors: scope of work, engagement terms, fee negotiation, timeline management, quality review, and performance evaluation.
Review all externally prepared returns and filings for accuracy, completeness, and optimization of filing positions before submission.
Manage the annual tax advisory budget; track spend against scope and challenge fees where deliverables don’t justify cost.
Continuously evaluate the in-house vs. outsourced compliance model — identify opportunities to bring high-value work internal or to restructure advisor engagements for better economics.
When specialized advisory is needed beyond the compliance advisor (e.g., transfer pricing, R&D credits, state incentive programs, M&A structuring), identify, engage, and manage those relationships independently.
Maintain a competitive awareness of alternative advisory firms to ensure the company has access to best-in-class tax advice and is not over-reliant on a single provider.
Income Tax Compliance Oversight
Oversee preparation of the consolidated federal income tax return and all related schedules by external advisors; perform detailed review and approve final filing.
Manage the Canadian federal tax return and ensure compliance with cross-border reporting requirements.
Oversee preparation and review of all state and local income/franchise tax returns across applicable jurisdictions.
Ensure all filing positions are defensible, well-documented, and aligned with the company’s risk tolerance.
Indirect & Specialty Tax Compliance
Manage sales and use tax filings across all applicable states.
Oversee premium tax return preparation and filing for insurance-regulated entities.
Prepare or supervise gross receipts, B&O, and other transaction-based tax filings.
Manage property tax filings and assessments; evaluate and challenge valuations where appropriate.
Ensure timely completion of various local tax returns and specialty filings.
Tax Provision & Financial Reporting
Calculate the monthly income tax provision (current and deferred) and prepare all related journal entries. This work is performed in-house and is not outsourced.
Manage federal and state estimated tax payment calculations and ensure timely remittance.
Maintain deferred tax asset/liability schedules; track and reconcile all significant book-to-tax differences.
Own the tax footnote disclosures for the annual audited financial statements; support the external audit on all tax-related matters.
Maintain book/tax difference tracking for intangible asset amortization in coordination with the Controller.
Coordinate with the Controller on deferred tax calculations related to equity compensation and goodwill/intangible amortization differences, using the Controller’s option amortization worksheet and valuation schedules as the source for monthly inputs.
Payroll & Employment Tax
Review the annual reconciliation between quarterly 941 filings and W-2s to ensure accuracy and compliance.
Review and advise on the taxability of deductions, supplemental pay, and new compensation additions as they arise, ensuring proper withholding treatment.
Advise on employment tax matters involving threshold-based withholding requirements (e.g., mandatory supplemental withholding rates for earnings exceeding $1 million).
Provide updated payroll tax rates and percentages to FP&A for use in the planning and forecasting platform.
Monitor changes in federal and state payroll tax requirements and communicate implications to Payroll and the Controller.
Equity Compensation & Intangible Asset Tax Matters
Coordinate with Payroll on the tax treatment of stock option exercises, terminations, and W-2 inclusions, including review of year-to-date earnings to ensure correct withholding rates are applied.
Maintain tax-basis amortization schedules for intangible assets and ensure alignment with valuation reports.
Tax Planning, Audits & Strategic Advisory
Lead all tax audits (federal, state, and local); manage information requests, negotiate with authorities, and drive matters to resolution.
Monitor and track all outstanding tax matters; maintain a tax contingency inventory and assess exposure.
Identify tax planning opportunities and engage appropriate advisory resources for structuring, credits, incentives, and rate optimization strategies.
Evaluate tax implications of new business initiatives, product structures, entity formations, and potential M&A transactions. Provide tax structuring recommendations directly to the CFO.
Monitor legislative and regulatory developments that could impact the company; communicate implications and recommended actions to the CFO and Controller.
Ensure compliance with casualty statutory basis reporting requirements and other state regulatory filings with tax implications.
Contribute to sponsor-level reporting and Board presentations on tax matters as needed.
Make Canadian subsidiary dividend recommendations to the CFO based on tax implications.
Process Improvement & Technology
Evaluate the current tax compliance workflow — both internal and external — for automation opportunities in filing preparation, data extraction, reconciliation, and calendar management.
Identify and implement tax technology tools (provision software, indirect tax engines, filing automation) to improve accuracy and reduce cycle time.
Maintain and update the comprehensive tax compliance calendar with clear ownership, deadlines, and escalation protocols across internal and external resources.
Develop standardized workpapers and documentation practices that support both audit readiness and institutional knowledge transfer.
Key Relationships:
As a direct report to the CFO, this role operates as a peer to the VP & Controller and the VP of FP&A. You will work closely with the Controller on all matters where tax intersects financial reporting, close, and compliance — including the monthly provision, deferred tax schedules, equity compensation entries, and statutory filings. The Controller owns the books; you own the tax.
You will collaborate with FP&A on tax-impacted forecasting and cash flow projections, including supplying updated payroll tax rates for the planning platform. You will work directly with HR/Payroll on employment tax matters, taxability determinations, and withholding compliance. You will also coordinate with Legal on entity structuring and regulatory filings. Externally, you will manage the company’s tax compliance advisors, engage specialized advisory firms as needed, and represent LegalShield in tax authority audits and examinations.
Education, Knowledge, and Experience
Required
CPA required; MST (Master of Science in Taxation) or JD/LLM in Taxation strongly preferred.
10+ years of progressive tax experience, including a mix of public accounting (Big 4 or national firm) and industry roles.
Deep expertise in corporate income tax compliance, multi-state taxation, and ASC 740 tax provision.
Hands-on experience managing indirect taxes (sales/use, gross receipts, property tax) across multiple jurisdictions.
Proven track record of managing external tax advisors — scoping work, controlling spend, holding firms accountable on quality and deadlines, and knowing when to bring work in-house vs. keep it outsourced.
Experience leading tax audits and managing tax authority relationships.
Strong ERP fluency; ability to extract, manipulate, and reconcile tax data from complex general ledger environments (Workday preferred).
Comfort operating in a PE-backed environment with sponsor-level reporting expectations and a bias for precision and speed.
Preferred
Cross-border tax experience (US/Canada).
Familiarity with tax technology platforms (OneSource, Vertex, Avalara, Corptax, or comparable).
Subscription or membership-based business model experience.
Experience with tax aspects of M&A transactions (due diligence, structuring, integration).
Exposure to equity compensation tax treatment (ISOs, NSOs, profits interests).
Experience managing and developing junior tax professionals.
Experience with insurance or premium tax compliance (regulated entity experience) is a plus, though this is a limited portion of the current workload given ongoing state deregulation.
What Success Looks Like in the First 12 Months
Completed a comprehensive inventory of all tax obligations, filing deadlines, external advisor scope, and spend — with no surprises.
Maintained and updated the existing tax compliance calendar, ensuring clear ownership for every filing and distinguishing internal vs. externally prepared items.
Delivered accurate, well-documented monthly tax provisions that the Controller and auditors can rely on without rework.
Evaluated the current external advisor model and delivered a recommendation to the CFO on the optimal in-house vs. outsourced mix — including cost, quality, and risk tradeoffs.
Established yourself as the senior tax authority in the organization — proactive, technically deep, and trusted by the CFO, Controller, and external advisors.
Completed a review of current filing positions and identified planning opportunities worth pursuing.
Identified at least two process automation or technology initiatives to reduce manual effort in tax compliance workflows.
Compensation & Location
Competitive base salary, annual bonus, and equity participation commensurate with experience. This is a location-flexible role. The accounting team is based in Ada, Oklahoma, and periodic travel (10–15% of the time) to Ada and other company locations will be required, with a heavier initial cadence during onboarding and transition.
FLSA Status
Exempt
Physical Requirements/ Work Environment
The work environment characteristics and physical demands described here are representative of these an employee encounters while performing the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.
Prolonged periods of sitting at a desk and working on a computer
Frequent use of hands and fingers to operate a computer keyboard, mouse, and telephone
Occasional standing, walking, bending, or reaching within the office environment
Ability to lift and/or move up to 10–15 pounds (e.g., files, office supplies, equipment)
Travel up to 10-15% of the time
Compensation for this position is $190,000 annually, based on experience and qualifications, with eligibility for a performance-based bonus opportunity.
Commitment to Equal Opportunity
PPLSI conforms to all the laws, statutes, and regulations concerning equal employment opportunities. We strongly encourage women, minorities, individuals with disabilities and veterans to apply to all of our job openings. We are an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to age, race, color, religion, sex, sexual orientation, gender identity, national origin, status as a protected veteran, and basis of disability or any other federal, state or local protected class. We prohibit retaliation against individuals who bring forth any concerns, orally or in writing, to the employer or the government, or against any individuals who assist or participate in the investigation of any concerns or otherwise oppose discrimination.
If you require a reasonable accommodation to complete the application process, please contact Human Resources at: [email protected].
Skills Required
- CPA required; MST or JD/LLM preferred
- 10+ years of progressive tax experience
- Deep expertise in corporate income tax compliance and ASC 740
- Experience managing external tax advisors
- Experience leading tax audits and managing tax authority relationships
- Strong ERP fluency; ability to extract tax data from general ledger
PPLSI Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about PPLSI and has not been reviewed or approved by PPLSI.
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Healthcare Strength — Medical, dental, and vision coverage begin on the first day with multiple plan options and FSA/HSA availability. Immediate eligibility and plan choice indicate robust core health coverage.
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Leave & Time Off Breadth — PTO increases with tenure and allows substantial rollover, and paid parental leave is offered. The ability to carry over a large PTO balance provides added flexibility for time away.
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Retirement Support — A dollar-for-dollar 401(k) match begins after one year, signaling meaningful long-term savings support.
PPLSI Insights
What We Do
We create services that protect and empower people. Our vision is to build a better world where access to justice and security is equal for every human — regardless of gender, race, orientation, education, social status, or personal wealth. PPLSI enables everyone to pursue their life – to worry less and live more – without the fear that a legal or privacy issue might bring it all crashing down. Our Mission PPLSI protects and empowers people with the tools and services needed to affordably live a just and secure life. Real Impact PPLSI is making a difference in the lives of our members. Through affordable legal services, we recovered and saved our members over $22 million in 2020. With our privacy and identity theft protection services, we saved our members an additional $5,000,000. With more than 1.8 million family members and 100,000 small business members, PPLSI brands provide access to technology and professional experts to make life better. Disrupting Justice We innovate and disrupt the traditional legal system – an expensive, complicated, and time-consuming system to make legal access simple, easy and affordable. In the same way that Uber forever changed the transportation industry, Amazon created a new way to shop for everyday goods and Netflix changed how people consume TV shows and movies; PPLSI is the disruptive force providing millions of people with access to the legal and identity protection services they deserve.
