Overview:
AgentSync is a leader in driving a contemporary insurance infrastructure experience. Our insurance compliance software connects the insurance industry to power growth, increase efficiency, and reduce risk. This is not your typical Customer Success Manager role. This is a high visibility, high value-add opportunity with a ton of trust, responsibility, and autonomy built-in right away. You will own the customer relationship end-to-end, driving measurable business outcomes while orchestrating internal teams to deliver exceptional value.

The Enterprise CSM will be an integral part of the Customer Success team, working with some of our highest value and most strategic customers to ensure they meet and exceed their goals with AgentSync. We’re looking for someone who thrives in high-stakes environments, can navigate complex customer dynamics with confidence, and isn’t afraid to step into challenging conversations—whether that’s with a C-suite customer or an internal executive.

What you’ll do:

Own and command the full customer lifecycle for ~30 of AgentSync’s most strategic accounts, driving measurable value, adoption, and expansion

Cultivate deep, trusted, and transparent relationships across all levels of the customer’s organization—from end-users and champions to C-suite decision-makers

Lead quarterly business reviews and executive conversations that tie product adoption to business impact.

Confidently manage escalations, serving as the first point of resolution and diffusing risk with minimal management support

Drive internal accountability, ensuring cross-functional teams deliver on commitments with urgency and clarity

Proactive and anticipatory mindset. A ‘plan’ vs. ‘react’ approach - takes pride in documenting and collaborating on customer engagement plans that serve as the backbone for our partnerships

Grow your insurance and compliance expertise to provide credible, strategic guidance on process improvements powered by AgentSync

Be an expert AgentSync’s full suite of products,



advising on best practices and use cases

Influence product, engineering, sales, and marketing by championing the voice of the customer and identifying opportunities to improve our product and customer experience

Contribute to the foundations of a world-class Customer Success function by creating and iterating on best practices, tools, and playbooks

Travel to meet with customers and conduct onsite executive business reviews

What you’ll bring:

10+ years of enterprise B2B SaaS experience in Customer Success

5+ years managing top-tier enterprise/strategic accounts—your company’s largest and most complex customers

Proven ability to navigate executive-level conversations with VP+ stakeholders in industries like insurance, financial services, compliance, or legal

Track record of successfully managing escalations and leading difficult conversations with both customers and internal teams

Strong ownership mentality—you take full responsibility for outcomes and hold customers and internal teams accountable

Natural influencer who can drive cross-functional alignment without formal authority

Exceptional communicator: skilled at simplifying complex solutions for customers and articulating customer needs to internal stakeholders

Problem-solver with high EQ: equally comfortable rolling up your sleeves in the details or zooming out to align on strategic goals

Actively using AI tools to improve the quality and speed of your work, and can speak to specific ways you’ve integrated them into how you get things done

Proactive, resourceful, and resilient—able to thrive in ambiguity while consistently delivering results.





Salesforce experience is a plus

Don’t meet every single requirement?

At AgentSync we are dedicated to building a diverse, inclusive and authentic workplace, so if you’re excited about this role but your past experience doesn’t align perfectly with every qualification in the job description, we encourage you to apply anyways. You may be just the right candidate for this or other roles.

Location
Our ideal candidate will live within 25 miles of our office in Denver, CO. Other states we’re able to consider candidates in CA, CO, CT, GA, IL, IN, KS, MA, MD, MI, MO, NC, NY, OR, TN, TX, UT, and WA.

Total Compensation

The following represents AgentSync’s reasonable estimate of the range of possible compensation for this role.

$150 - 180K base salary

OTE $170 - 200K

Equity in the form of stock options

Health Benefits

Medical - Multiple Cigna plans to choose from, with up to 100% employer paid premiums for you and up to 80% for your dependents

Dental - Multiple Cigna plans with up to 80% employer paid premiums for you and your dependents

Vision - 80% paid premium plan for you and your dependents

Employee Assistance Plan, Life & AD&D; Insurance

Financial Benefits

401(k) retirement savings plan

HSA employer contributions

Other Benefits

Flexible PTO

12 paid holidays per year

12 weeks parental leave w/generous return to work stipend

Candidates: AgentSync Recruiting & Talent teams will only communicate with you using @agentsync.ioemail addresses. When you receive communication from AgentSync, check the email address domain to ensure you’re connected with our team (and not a scammer!).

We are not able to consider candidates who require a work visa now or in the future.

E-Verify: AgentSync participates in the federal E-Verify program. As required, we will verify the identity and employment eligibility of all newly hired employees through E-Verify.

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📌 Enterprise Customer Success Manager (Ontario)
🏢 AgentSync
📍 Ontario