Senior Delivery Manager - SaaS Migration

About Sycle

Sycle is a market-leading global SaaS company with the mission of facilitating the delivery of better hearing to the world. Founded in 2001, we have grown to be the leading practice management solution for audiology (hearing care) providers, with more than 65% market share. The Sycle practice management solution frees up valuable time so our customers can grow their businesses through delivering high quality patient care and exceptional services that delight their customers. Small hearing care practices and some of the largest retailers utilize our software in 13 countries worldwide.

The Sycle team is 120 strong. We are headquartered in Lone Tree, Colorado with a large remote workforce across the US and Canada. We are always on the lookout for exceptional talent to help us build and deliver market-leading tools that make a difference for our customers. Check out our job listings and apply!

Position Overview

Sycle is seeking a results-driven Senior Delivery Manager to lead product delivery and technical strategy for one of our strategic enterprise accounts. This high-visibility role focuses on driving a multi-year migration strategy—transitioning a major partner from a customized, legacy system to our flagship SaaS platform, all while balancing ongoing feature delivery, security remediation, and integration needs. The role is open to candidates from British Columbia. 

You will operate at a fast pace, balancing deep technical architecture (APIs, integrations, data migrations) with strategic account management and cross-functional leadership. If you thrive in fast-moving environments, possess strong clinical domain knowledge, and handle ambiguity with composure, this position offers an exceptional opportunity to make a massive impact.

Key Responsibilities

• Enterprise Account Product Leadership: Own the strategic product relationship for a key enterprise account, setting client expectations, communicating frequent progress updates, and building executive trust.
• Legacy-to-SaaS Migration Strategy: Lead third-party integration planning, gap analysis, and system/data migrations from a highly customized legacy system to Sycle’s modern SaaS platform.
• Technical & Platform Thinking: Deeply understand system architecture, APIs, DevOps/infrastructure dependencies, and data flows to guide engineering teams and make informed trade-off decisions.
• Fast-Paced Prioritization & Execution: Successfully balance multiple concurrent initiatives spanning client features, technical debt, integrations, and platform stability in an environment of shifting client priorities.
• Ambiguity to Execution: Take complex, unstructured customer problems, evaluate underlying technical constraints, and deliver clear product requirements that maximize customer value.
• Cross-Functional Collaboration: Partner closely with Strategic Account Management, Engineering, and Business Analysts to optimize delivery practices, sprint velocity, and team efficiency.
• Excellent Communication: Ability to translate complex technical concepts into clear prose and concise client updates.

Qualifications

• Audiology & Hearing Care Domain Expertise: Deep understanding of audiology, clinical workflows, and hearing care clinic operations is strongly preferred / highly important. (Broader enterprise digital health experience considered).
• Enterprise Account Management: Proven history managing strategic enterprise software accounts and presenting to external client stakeholders and executives.
• Deep Technical Acumen: Hands-on experience working directly with engineering teams on APIs, data architecture, security remediation, and complex system integrations with minimal technical guidance.
• Resilience & Conflict Management: Exceptional emotional intelligence, stress management, and composure in high-pressure environments where scope and priorities evolve rapidly.
• Track Record in Platform Migrations: Experience leading complex software migrations or enterprise re-platforming initiatives.
• Process & Delivery Optimization: Proven ability to establish clear delivery practices, manage dependencies, and drive predictability across cross-functional teams.
• AI-Augmented Delivery & Strategy: Proactively integrate AI productivity tools into daily practices to speed up artifact creation, optimize complex system gap analysis, and quickly translate unstructured client needs into actionable product specifications.

Benefits

• Medical, Dental, and Vision: Sycle pays employee-only premiums at 100% for base plans.
• Flexible Spending Accounts (FSA): Pre-tax options for Health ($3,400/yr) and Dependent Care ($7,500/yr).
• Life & Disability: Voluntary Life/AD&D; Short-Term (60% up to $2,000/week) and Long-Term (60% up to $7,500/month) Disability.
• 401(k) with Matching: 100% match on the first 3% of salary deferrals, plus 50% match on the next 2%—with no vesting schedule.
• Time Off: Paid holidays (~14 days), 12 vacation days, 4 personal days, and 9 sick days.
• Perks: $50/month internet stipend and tuition reimbursement.

How to Apply

To apply, please submit your resume. If you’re going to submit a cover letter please focus on how your previous experience relates to this role and why you would be a good fit. Please include your LinkedIn profile in both your resume and in the designated application field. 

Compensation Note: Salary ranges reflect our national pay band. Offers are determined based on the successful candidate's geographic location, local cost of living, and experience.