Senior Sales Advisor

Milliman Financial Risk Management; Chicago (IL); Hybrid; USD 138,000 - 227,000; Full time

Benefits offered by this job

Medical/Dental/Vision

401(k) matching

Discretionary bonus

PTO 15 days

Holidays 10+

Family building benefits

Paid parental leave

Job summary

Milliman Financial Risk Management in Chicago, IL is seeking an experienced enterprise software sales leader to drive growth of our actuarial modeling and technology platform across the life insurance market.

You will build relationships with insurers, lead opportunities from discovery through negotiation and close, and collaborate with Milliman actuaries, product leaders, and technology specialists to advance modernization and deliver measurable business value.

Qualifications

• Seven+ years in enterprise software sales or related field.
• Experience selling to senior executives and navigating buying committees.
• Background in SaaS, cloud platforms, APIs, modernization, or related solutions.

Responsibilities

• Win new clients by identifying and developing software opportunities across targeted life insurers.
• Build relationships with Chief Actuaries, CIOs, and other technology decision-makers.
• Lead opportunities from initial conversation through discovery, demonstration, evaluation, negotiation and close.
• Partner with Milliman actuaries, product leaders and tech specialists to bring the right expertise into each opportunity.
• Develop strategic account plans and maintain a strong pipeline of opportunities.
• Represent Milliman at industry events to raise brand visibility.

Skills

Enterprise software sales

Executive stakeholder engagement

Complex deal negotiation

Account development

SaaS/cloud selling experience

Education

Bachelor's degree or equivalent

Job description

We are seeking an experienced enterprise software sales leader to drive growth of a leading actuarial modeling and technology platform across the life insurance market. Our technology has evolved alongside the needs of insurers, advances in actuarial practice, and emerging technologies. Today, innovations in cloud computing, GPU processing, artificial intelligence, analytics, and optimization are creating new opportunities to help insurers modernize decision-making, improve efficiency, and unlock greater business value.

The Senior Sales Advisor will bring that vision to market, build relationships with insurers that may not know Integrate today, and turn interest in actuarial modernization into strategic software opportunities.

You will:

• Win new clients for by identifying and developing software opportunities across targeted life insurers


• Build senior relationships with Chief Actuaries, CIOs, actuarial modeling leaders and other technology decision-makers.


• Create opportunities before a formal RFP or software replacement process begins.


• Generate excitement around the platform vision and the future of actuarial technology.


• Identify triggers such as technology modernization, regulatory change, cloud initiatives, AI strategies, and evolving actuarial operating models.


• Lead clients from initial conversation through discovery, demonstration, evaluation, commercial negotiation and close.


• Partner with Milliman actuaries, product leaders and technology specialists to bring the right expertise into each opportunity.


• Develop strategic account plans and maintain a strong pipeline of competitive software opportunities.


• Keep the pipeline current, adjusting account strategy as deals evolve, and keeping key internal stakeholders informed on progress and next steps.


• Bring client and competitive intelligence back into the product and leadership teams, helping shape product direction and sharpen our competitive edge.


• Represent Milliman at industry events, conferences, and executive forums — building the brand's visibility, strengthening relationships with key industry voices, and positioning Milliman as a thought leader in actuarial technology

Qualifications Required

• Bachelor’s degree in business, finance, marketing, operations, or related field, or equivalent professional experience.


• Seven or more years of experience in enterprise software sales


• Proven success selling complex solutions with deal sizes ranging from $200K to $5M+.


• Relentless drive to win new business, backed by a demonstrated track record in business development.


• Experience selling to executive stakeholders and navigating complex buying committees.


• Background in SaaS, cloud platforms, APIs, modernization, digital transformation, managed services, or related solutions.

Experience and Soft Skills Required

• Strong experience developing new accounts and creating demand rather than relying on inbound opportunities.


• Experience selling into life insurance or the broader insurance industry.


• Ability to engage senior executives and communicate a compelling technology vision.


• Experience navigating complex, multi-stakeholder enterprise software decisions.


• Strong commercial, negotiation, and account development skills.


• Intellectual curiosity and comfort discussing cloud, AI, analytics and technology modernization.


• Ability to effectively leverage technical and subject matter experts throughout the sales process.


• Insurance, reinsurance, actuarial, risk, finance, or capital markets experience is strongly preferred.


• An inquisitive, self-starter who thrives in ambiguity and familiar environments.

Location

Candidates hired into this role will be required to work in-person in the Milliman office in Chicago, IL on a weekly basis, but flexible work arrangements will be considered.

Compensation

The salary range for this role is $137,828 - $227,445 depending on a combination of factors, including, but not limited to, education, relevant work experience, qualifications, skills, certifications, location, etc.

We offer a comprehensive benefits package designed to support employees’ health, financial security, and well-being. Benefits include:

• Medical, Dental and Vision – Coverage for employees, dependents, and domestic partners.


• Employee Assistance Program (EAP) – Confidential support for personal and work-related challenges.


• 401(k) Plan – Includes a company matching program and profit-sharing contributions.


• Discretionary Bonus Program – Recognizing employee contributions.


• Flexible Spending Accounts (FSA) – Pre-tax savings for dependent care, transportation, and eligible medical expenses.


• Paid Time Off (PTO) – Begins accruing on the first day of work. Full-time employees accrue 15 days per year, and employees working less than full-time accrue PTO on a prorated basis.


• Holidays – A minimum of 10 paid holidays per year.


• Family Building Benefits – Includes adoption and fertility assistance.


• Paid Parental Leave – Up to 11 weeks of paid leave for employees who meet eligibility criteria.


• Life Insurance & AD&D – 100% of premiums covered by Milliman.


• Short-Term and Long-Term Disability – Fully paid by Milliman.

All qualified applicants will receive consideration for employment, without regard to race, color, religion, sex, sexual orientation, national origin, disability, or status as a protected veteran.