Enterprise Sales Director, Financial Services

Enterprise Sales Director, Financial Services

New logo | Banking, credit unions, insurance, mortgage, and wealth management

About SundaySky

SundaySky is a pioneer in AI-powered video personalization, transforming how enterprise brands - particularly in banking, financial services, and insurance - connect with their customers. Our platform turns customer data into personalized video experiences at scale, guiding customers and members through the moments that matter most: account onboarding, mortgage milestones, retirement decisions, digital banking adoption, and more.

The results are measurable. Financial institutions use SundaySky to reduce cost-to-serve, cut attrition, accelerate digital adoption, and grow product depth. T. Rowe Price saw 550% more savings contribution increases among participants who watched their personalized SundaySky video versus those who did not.

SundaySky is backed by Clearhaven Partners, a Boston-based private equity firm focused exclusively on software and technology businesses. That partnership gives us the operating resources and strategic support to grow fast and take share. Learn more at sundaysky.com. For creating requisitions 'from scratch'

The opportunity

We are building a new logo sales team that plays to win. This is a quota-carrying hunter role for someone who wants to open doors at large banks, credit unions, insurers, mortgage lenders, and wealth managers - and turn them into SundaySky customers.

You will own a defined territory of target accounts, build your own pipeline, and run complex, multi-stakeholder deals from first meeting to signature. You will sell to CX, marketing, digital, and product leaders who are under pressure to deliver better customer experiences at lower cost - and you will win by proving the business case, not by pitching features.

If you are competitive, persistent, and measure yourself by the number on the board, we want to talk to you.

What you will do

• Hunt new logos: Prospect and open net-new enterprise accounts across banking, credit unions, insurance, mortgage, and wealth management. Self-source a meaningful share of your pipeline through disciplined outbound - calls, email, LinkedIn, events, and partners - working alongside our SDR team.

• Sell to outcomes, not features: Uncover each prospect's business goals and objectives - onboarding, retention, call deflection, digital adoption, cross-sell, participant outcomes - and build a quantified business case that ties SundaySky directly to them.

• Multithread every deal: Map the buying committee and build relationships across CX, marketing, digital, product, data and IT, compliance, and procurement. Develop champions, secure an executive sponsor, and never let a deal rest on a single contact.

• Run a rigorous sales process: Qualify hard, drive stage progression and deal velocity, and navigate the security reviews, legal redlines, and procurement processes that come with selling into regulated institutions.

• Juggle many priorities at once: Manage a full pipeline of early- and late-stage opportunities across multiple accounts at the same time - without dropping the ball on any of them.

• Own your number: Keep Salesforce current, forecast accurately, and come to weekly pipeline reviews ready to commit and deliver.

• Land deals that grow: Scope every deal for success - clear value metrics, an engaged executive sponsor, and a committed data path - and hand off cleanly to Customer Success so new customers renew and expand.

• Leverage the ecosystem: Co-sell with channel and referral partners across the banking and credit union ecosystem to open doors and accelerate deals.

How you will be measured

We run a performance culture with clear, visible metrics. Success in this role means:

• New logo bookings against quota

• Self-sourced pipeline generation and pipeline coverage

• Meetings set and held, and multithreaded engagement within target accounts

• Stage progression, deal velocity, and win rate

• Forecast accuracy

REQUIREMENTS

Must-haves

• 7+ years of quota-carrying enterprise B2B SaaS sales experience, with a consistent track record of meeting or exceeding quota. Stack rankings, President's Club, and attainment history you can walk us through.

• Direct experience selling into banking, financial services, insurance, and/or mortgage organizations. Wealth management and retirement experience is a plus.

• A proven new logo hunter: you have built pipeline from scratch and closed six-figure deals with $1B+ revenue organizations through long, complex sales cycles.

• Experience selling to CX, marketing, digital, and product leaders, and translating capabilities into ROI they can take to their CFO.

• Elite discovery skills and a natural instinct for multithreading across large buying committees.

• The ability to multitask and manage many priorities, accounts, and deal stages at once.

• Experience navigating procurement, security, and legal reviews in regulated industries.

• Excellent written and verbal communication; executive presence with senior buyers.

• BA/BS or equivalent experience.

Strong plus

• 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 the financial services tech stack - core banking, digital banking, loan origination, CRM, and marketing automation (Salesforce, Marketo, 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.

How you are wired

• Competitive: You want to win, and you hate to lose. You know where you stand on the leaderboard, and you play to win - not to avoid losing.

• Hungry: You are motivated by building something and by earnings that track your performance. Average is not a goal.

• Persistent: A "no" or a "not now" is the start of the conversation. You follow up, find another way in, and stay with it until you get an answer.

• Accountable: You own your number, your pipeline, and your activity. No excuses, no surprises.

• Coachable: You learn fast, take feedback, and adapt your approach when the data says to.

• Team-first: You win as one team with SDRs, Customer Success, Product, and Marketing, and you live our values: collaboration, empathy, excellence, innovation, and simplicity.

Compensation and benefits

$200K-$225K OTE with a 50/50 base and variable split, based on experience. Benefits include health, vision, and dental insurance, 401(k) match, and stock options.

This is a remote position.

SundaySky is an equal-opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. Different makes us better.