Enterprise Sales Director, Financial Services

SundaySky•New York, NY

19h•Remote

About The Position

SundaySky is hiring a quota-carrying, new-logo enterprise sales hunter to sell its AI-powered video personalization platform to large banks, credit unions, insurers, mortgage lenders, and wealth managers. The role owns a defined territory of target accounts, builds pipeline—including a meaningful share through self-sourced outbound—and manages complex, multi-stakeholder sales from initial meeting through signature. The salesperson engages CX, marketing, digital, and product leaders, builds quantified business cases tied to customer outcomes, and navigates regulated-industry sales processes. The role is remote. Success is measured by new-logo bookings against quota, self-sourced pipeline generation and coverage, meetings and multithreaded account engagement, stage progression, deal velocity, win rate, and forecast accuracy. The position requires maintaining accurate Salesforce records and forecasts, collaborating with SDRs and partners, and handing off well-scoped deals to Customer Success for renewal and expansion.

Requirements

At least 7 years of quota-carrying enterprise B2B SaaS sales experience and a consistent record of meeting or exceeding quota.
Direct sales experience with banking, financial services, insurance, and/or mortgage organizations.
A demonstrated new-logo hunting track record, including building pipeline from scratch and closing six-figure deals with organizations with $1B+ in revenue through long, complex sales cycles.
Experience selling to CX, marketing, digital, and product leaders and translating capabilities into ROI business cases for CFOs.
Strong discovery skills and an ability to multithread across large buying committees.
Ability to manage multiple priorities, accounts, and deal stages simultaneously.
Experience navigating procurement, security, and legal reviews in regulated industries.
Excellent written and verbal communication skills and executive presence with senior buyers.
BA/BS degree or equivalent experience.

Nice To Haves

Wealth management and retirement experience.
Experience selling personalized or interactive video, digital banking platforms, or customer experience technology to financial institutions.
Established relationships with CX, digital, and marketing leaders at banks, credit unions, insurers, or mortgage lenders.
Familiarity with financial services technology, including core banking, digital banking, loan origination, CRM, and marketing automation platforms such as Salesforce, Marketo, and Snowflake.
Training in a structured sales methodology such as MEDDIC/MEDDPICC, Challenger, or Command of the Message.
Experience co-selling with channel, referral, or technology partners.

Responsibilities

Prospect and open net-new enterprise accounts across banking, credit unions, insurance, mortgage, and wealth management.
Self-source a meaningful share of pipeline through outbound calls, email, LinkedIn, events, and partners, working with the SDR team.
Discover prospects’ business goals and develop quantified business cases that connect SundaySky to outcomes such as onboarding, retention, call deflection, digital adoption, cross-sell, and participant outcomes.
Map buying committees and build relationships across CX, marketing, digital, product, data and IT, compliance, and procurement; develop champions and secure an executive sponsor.
Qualify opportunities, drive stage progression and deal velocity, and navigate security reviews, legal redlines, and procurement processes.
Manage early- and late-stage opportunities across multiple accounts and priorities.
Maintain current Salesforce records, forecast accurately, and participate in weekly pipeline reviews ready to commit and deliver.
Scope deals for success with clear value metrics, an engaged executive sponsor, and a committed data path; hand off new customers to Customer Success.
Co-sell with channel and referral partners across the banking and credit union ecosystem.
Meet performance measures for bookings, pipeline, meetings, account engagement, stage progression, deal velocity, win rate, and forecast accuracy.