Enterprise Account Executive at Literati

Chicago, Illinois, United States

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Not SpecifiedCompensation

Senior (5 to 8 years)Experience Level

Full TimeJob Type

UnknownVisa

InsuranceIndustries

Requirements

Enterprise software sales experience with a strong track record of closing $1M+ ARR deals
Proven success selling to insurance carriers, MGAs, or large brokerages
Deep understanding of insurance technology ecosystems (policy admin, claims, billing, digital engagement)
Strong network of relationships in the P&C insurance market
Extreme sense of ownership, urgency, and customer obsession, thriving in a Series-A startup environment
Excellent storytelling, executive presence, and negotiation skills
Ability to collaborate cross-functionally with product, engineering, and customer success
10+ years of experience selling enterprise software into insurers and large carriers

Responsibilities

Own the full enterprise sales cycle: prospecting, qualification, solution positioning, negotiation, and close
Develop and execute a territory/account plan focused on top-tier insurers and carriers
Build and maintain C-level relationships across business (Claims, Underwriting, Operations) and technology (CIO, CTO, CDO) functions
Collaborate with Solutions Engineering and Product to tailor AI-driven demos and proofs-of-concept
Navigate complex procurement processes in insurance enterprises, including RFPs and multi-stakeholder evaluations
Achieve and exceed quarterly/annual sales quotas
Contribute customer insights to influence Liberate’s product roadmap
Represent Liberate at key industry events, conferences, and roundtables

Skills

Key technologies and capabilities for this role

Enterprise Software SalesQuota CarryingC-level RelationshipsProspectingQualificationSolution PositioningNegotiationClosing DealsTerritory PlanningRFPsProofs-of-ConceptInsurance TechnologyClaimsUnderwritingPolicy Admin

Questions & Answers

Common questions about this position

What are the compensation details for this Enterprise Account Executive role?

The role offers a competitive salary with performance-based commissions and equity options.

Is this a remote position, or does it require office time?

This is a hybrid role requiring 2 days per week in-office, available in Columbus, Chicago, Dallas, Atlanta, Miami, Los Angeles, San Francisco, or Boston, with flexible work environment and remote options.

What are the key qualifications and skills required for this position?

Must have 10+ years of enterprise software sales experience closing $1M+ ARR deals to insurance carriers, deep understanding of insurance technology ecosystems, strong network in P&C insurance, and excellent storytelling, executive presence, negotiation, and cross-functional collaboration skills.

What is the company culture like at Liberate Innovations?

The company has a collaborative and innovative culture, thriving in a Series-A startup environment with direct access to leadership, product, and customer success teams.

What makes a strong candidate stand out for this role?

Candidates with a proven track record of closing $1M+ ARR deals to insurers, strong C-level networks in P&C insurance, and experience thriving in high-growth startups with extreme ownership and executive presence will stand out.

Literati

Curated book subscription service for all ages

About Literati

Literati offers a subscription service for curated book selections aimed at both adults and children. Each month, subscribers receive a new hardcover book chosen by influential figures, known as Luminaries, from various fields such as business, sports, and the arts. This approach provides readers with enriching and inspiring content. For children, Literati features a 'try before you buy' option, allowing parents to receive a selection of expertly reviewed books to ensure quality and age-appropriateness. The company differentiates itself by combining celebrity involvement with expert curation, appealing to those seeking intellectual and inspirational reading experiences. Literati's goal is to foster a love for reading through high-quality literature while generating revenue through subscription fees and book sales.

Austin, TexasHeadquarters

2017Year Founded

$89.5MTotal Funding

SERIES_BCompany Stage

Education, Consumer GoodsIndustries

201-500Employees

Benefits

Health Insurance

Dental Insurance

Vision Insurance

401(k) Retirement Plan

401(k) Company Match

Short-term Disability Insurance

Parental Leave

Flexible Work Hours

Unlimited Paid Time Off

Company Equity

Risks

Increased competition from companies like Book of the Month challenges Literati's market share.

Celebrity involvement risks brand reputation if associated figures face controversies.

Integration challenges from Follett Book Fairs acquisition may disrupt Literati's operations.

Differentiation

Literati offers curated book selections with celebrity involvement, enhancing its unique market position.

The 'try before you buy' model for children's books sets Literati apart from competitors.

Literati's platform includes exclusive content and discussions, enriching the reader's experience.

Upsides

Rising interest in personalized content boosts demand for Literati's curated book services.

AI-driven personalization can enhance Literati's book selection process, improving customer satisfaction.

Celebrity and influencer marketing trends align with Literati's Luminary-curated adult book offerings.

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