New

Senior Director of LegalTech

Cotton & Company LLP
paid time off, paid holidays, sick time, tuition reimbursement, flex time, 401(k)
United States, Virginia, Alexandria
333 John Carlyle Street (Show on map)
Feb 23, 2026
Description LegalTech Senior Director - Remote What to expect when you join Sikich Team members at Sikich have a lot in common while also being part of a rich and diverse group of contributors, creating a distinct and thriving culture. Chief among our commonalities is a desire for growth and a shared unity of purpose in our professional lives. We believe that through diverse perspectives, challenging the status quo and rewarding action, we accelerate innovation and drive growth - for our clients, for ourselves and for our communities. The professional services landscape continues to evolve. For Sikich, this means we have an opportunityto furthercement our leadership position in this industry and continue to grow our organization in increasingly exciting ways. This growth is meaningful for every team member at our firm because larger companies simply see more interesting client opportunities and can attract impressively talented individuals like you. Through a dedicated focus on key business priorities and intentionally creatinga rewardingemployee experience, Sikich has developed into a highly regarded provider of professional services and a sought-after employer of choice. Do you want to work with other skilled practitioners and serve clients in a way that makes a difference? Are youseeking a supportive environment backed by a deep and extensive set of skillsets? Are you ready to make an impact and be acknowledged for your contributions? If youansweredyes to these questions, we see a mutually beneficial and gratifying relationship on the horizon! *Are you ready to grow with us?* About the Role:As the Senior Director of the LegalTech Practice, you will lead a multi-million-dollar services business with full accountability for revenue, margin, vendor relationships, and delivery performance. You will define the practice's service strategy and drive disciplined growth in close collaboration with sales and partner ecosystems. What will you do in this role? Provide strategic and operational leadership to the LegalTech Practice, ensuring disciplined execution, forecast accuracy, vendor trust stewardship, and margin performance while driving sustainable growth. Own executive-level vendor relationships and QBR cadence, ensuring alignment on pipeline, delivery performance, and co-sell strategy. Own the LegalTech practice P&L, driving revenue growth, margin expansion, and disciplined financial performance. Recruit, develop, and hold accountable for a high-performing team of consultants and leaders. Manage resource allocation, including staffing assignments, project budgets, and resource utilization, to maximize efficiency and profitability. Collaborate with senior leadership to define the practice's service mix, capability roadmap, and growth priorities in alignment with broader industry strategy. What do you need to succeed in this role? 8+ years of progressive leadership experience within IT consulting or vertical SaaS services, ideally including LegalTech or adjacent regulatedindustry practice Proven experience leading a multi-million-dollar IT consulting or professional services practice, preferably in legal or vertical Saas services. Demonstrated ability to drive revenue growth within a partner-led or channel-driven model. Excellent communication, interpersonal, and negotiation skills. Strong financial acumen with experience owning P&L performance. Familiarity with emerging technologies, including AI-driven capabilities, and ability to incorporate them into service offerings where strategically appropriate. About Sikich Sikichoffers the public and private sectors a diverse platform of professional services across consulting,technologyand compliance. Highly specialized and hands-on teams deliver integrated solutions rooted in deep industry experience. Our approach is strategically and thoughtfully designed to help our clients,teamsand communities accelerate success. Sikich has approximately 2,000 team members and operates across North America, EMEA and APAC. Sikich Total Rewards Our team members enjoy expansive benefits ranging from competitive compensation and insurance options to wellness programs and a flexible time off policy, to name only a few. Sikich also takes pride in prioritizing team members' health, total wellbeing and time spent with family, friends and in the pursuit of personal goals, hobbies, and endeavors. Some examples of our many benefits: Sikich maintains a Flexible Time Off (FTO) Policy. We encourage every full-time employee, as your role permits, to utilize paid time off (personal time, mental/physical health care, vacation, sick leave, etc.). Waiting for time off to accrue is common at other companies. At Sikich, you do not have to wait for this benefit to kick in. FTO is activated on your first day with our organization. Sikich will also recognize paid holidays during the year and strives to permit employees to have time off the last week of the calendar year when client and project work permits. Sikich offers a comprehensive wellness program to engage, challenge and empower team members to take responsibility for their wellbeing. Activities can be tracked through our wellness provider to obtain gift cards and other rewards. We also offer: Flexible work arrangements Health, dental, vision, life, and accident/death/disability insurance options HSA employer contribution Nine (9) paid holidays annually. A robust paid Parental Bonding Leave program covering birth, adoption, and foster children. 401(k) with employer contributions CPA bonus with four (4) paid exam days & four (4) paid study days. Tuition reimbursement Generous employee referral bonus program Client referral bonus program Pet insurance FORCE - Sikich community volunteer program enabling each team member to use up to four hours of paid time annually to volunteer and make a difference in their localcommunities. *Official correspondence will come from a Sikich.com email address and applicants/candidates are invited to contact us directly to verify communications. Want to learn more? Visit ourCareers websiteorGlassdoor profile. Sikich is an Equal Opportunity Employer M/F/D/V Sikich currently practices in an alternative practice structure in accordance with the AICPA Professional Code of Conduct and applicable law, regulations, and professional standards. Sikich CPA LLC is a licensed CPA firm that provides audit and attest services to its clients. Sikich LLC has a contractual arrangement with Sikich CPA LLC under which Sikich LLC provides Sikich CPA LLC with professional and support personnel and other services to support Sikich CPA LLC's performance of its professional services, and Sikich CPA LLC shares certain client information with Sikich LLC with respect to the provision of such services.