Enterprise Sales Director, Financial Services

SundaySky•New York, NY

3h•$200,000 - $225,000•Remote

About The Position

SundaySky is hiring a quota-carrying Enterprise Sales Director to win new enterprise customers across banking, credit unions, insurance, mortgage, and wealth management. The role owns a defined territory of target accounts, builds pipeline through outbound prospecting and partner relationships, and manages complex, multi-stakeholder sales from initial meeting through signature. The salesperson engages CX, marketing, digital, product, and other leaders, and establishes a quantified business case tied to customer outcomes rather than product features. The role requires disciplined pipeline and forecast management, navigating security, legal, and procurement processes at regulated institutions, and coordinating with SDRs, channel and referral partners, and internal teams. Deals should be scoped for customer success, with clear value metrics, executive sponsorship, and a committed data path, before handoff to Customer Success. Performance is measured by new-logo bookings against quota, self-sourced pipeline and coverage, meetings, multithreaded engagement, stage progression, deal velocity, win rate, and forecast accuracy. SundaySky describes itself as a pioneer in AI-powered video personalization for enterprise brands, particularly in financial services. The position is remote. Compensation is $200,000–$225,000 OTE, with a 50/50 base and variable split based on experience.

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.
Demonstrated new-logo hunting experience, including building pipeline from scratch and closing six-figure deals with organizations exceeding $1 billion in revenue through long, complex sales cycles.
Experience selling to CX, marketing, digital, and product leaders and translating capabilities into ROI for CFOs.
Strong discovery skills and ability to multithread across large buying committees.
Ability to multitask and manage multiple priorities, accounts, and deal stages.
Experience navigating procurement, security, and legal reviews in regulated industries.
Excellent written and verbal communication and executive presence with senior buyers.
BA/BS degree or equivalent experience.
Competitive, hungry, persistent, accountable, coachable, and team-first approach, as described in the posting.

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 activity and work alongside the SDR team.
Discover prospects’ business goals and build quantified business cases connecting 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 a full pipeline of early- and late-stage opportunities across multiple accounts and priorities.
Maintain Salesforce, forecast accurately, and participate in weekly pipeline reviews prepared to commit and deliver.
Scope deals for success with clear value metrics, an engaged executive sponsor, and a committed data path, then hand off to Customer Success.
Co-sell with channel and referral partners across the banking and credit union ecosystem.
Meet performance measures for new-logo bookings, self-sourced pipeline generation and coverage, meetings, multithreaded engagement, stage progression, deal velocity, win rate, and forecast accuracy.