[Hiring] Enterprise Sales Director @SundaySky

Role Description

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.

Responsibilities

• 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

• 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

Qualifications

• 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.