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Destify

Director Of Sales

Destify, Chicago, Illinois, United States, 60290

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We are Destify! We focus on our people, our culture, and our technology. We have completely changed the way couples book their destination weddings by combining exceptional technology and service. Our team and platform streamlines every step of the destination wedding journey, from discovery to guest booking to travel.

You are a process-obsessed, performance-driven sales leader with SaaS‑style rigor and hospitality‑grade empathy. You’ll run a remote team that turns complex, emotionally charged decisions into confident bookings and bring the operational mindset of a RevOps pro to everything you touch.

What You’ll Do Sales Leadership & Strategy

Build, lead, and scale a distributed sales team focused on measurable revenue growth

Design and execute a structured, data-backed sales process optimized for long‑funnel conversions

Forecast accurately, manage pipeline health, and drive quota attainment through metrics and accountability

Coaching & Performance

Implement a behavioral coaching framework that blends data, CRM discipline, and consultative storytelling

Hold weekly 1:1s and use dashboards to diagnose performance and reinforce winning habits

Elevate team standards with clear expectations, consistent follow‑through, and visible results

Sales Operations & Enablement

Own HubSpot CRM sales setup, reporting, and optimization to ensure data integrity and visibility

Apply Revenue Ops principles to streamline processes, lead flow, and funnel reporting

Collaborate with Marketing and Leadership to improve workflow performance, lead quality, and experience alignment

Build and refine dashboards, workflows, and automations that enhance sales productivity and conversion efficiency

Evaluate and deploy sales-enablement tools that improve efficiency and clarity

Cross‑Functional Collaboration

Partner with Marketing, Leadership, and internal stakeholders to align the full revenue funnel

Provide performance insights that inform strategy, messaging, and overall user experience to drive sales

Requirements

5+ years leading high‑performing virtual sales teams

Deep expertise in HubSpot or SalesForce (required) and familiarity with sales systems frameworks

Proven record in SaaS, tech‑enabled services, or high‑consideration B2C environments

Strong analytical mindset: you forecast, model, and measure everything

Comfortable selling emotionally driven products through structured, consultative processes

Exceptional communicator, clear, direct, and data‑literate

Bachelor’s degree or equivalent experience

Why Destify

$135,000-185,000 base + bonus structure

Flexible Paid Time Off and Paid Parental Leave

Caribbean travel perks to reward high performers

Fully remote work environment

Comprehensive benefits – Medical, Dental, and Vision

401(k) with company match

You’ll Succeed Here If You…

Think like a SaaS operator but sell like a concierge

Love turning ambiguity into process

Treat CRM data and attribution as the language of leadership

Excel at leading and growing a successful sales team

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