Director of Mid-Market Sales, Iterable
North America, West Region
$336-456k
OTE
Plus equity. OTE is includes annual base salary and target variable pay (actual payout is subject to the percentage attainment of specific sales goals)
AI-powered customer communication platform
Be an early applicant
AI-powered customer communication platform
501-1000 employees
Be an early applicant
$336-456k
OTE
Plus equity. OTE is includes annual base salary and target variable pay (actual payout is subject to the percentage attainment of specific sales goals)
501-1000 employees
Company mission
To connect people with products that bring them joy.
Role
Who you are
- We’re looking for someone who thrives in fast-paced environments, enjoys coaching as much as closing, and believes that developing people is the most scalable way to drive results
- 3+ years leading high-performing quota-carrying SaaS sales teams in a fast-paced technology company
- 5+ years of successful enterprise software sales experience prior to moving into leadership
- Demonstrated success personally closing complex software opportunities ranging from approximately $100K to $500K+ ARR involving multiple stakeholders and executive decision-makers
- Experience coaching teams using MEDDPICC (or a comparable enterprise qualification methodology)
- Experience developing consultative sellers through Challenger Sale or other value-based sales methodologies
- Consistent track record of building teams that exceed quota and improve performance over time
- Strong forecasting discipline with a history of delivering predictable revenue outcomes
- Excellent executive presence with the ability to influence customers, internal stakeholders, and senior leadership
- Strong analytical mindset with the ability to diagnose pipeline risk, identify trends, and drive measurable improvements
- Experience working within Salesforce, Gong, Clari, and modern sales technology platforms
- Excellent communication, coaching, and leadership skills
- Bachelor’s degree preferred
What the job involves
- Iterable is looking for an experienced sales leader to build, coach, and scale a high-performing Mid-Market Sales team. As Director of Mid-Market Sales, you will lead a team of Account Executives responsible for acquiring strategic customers across North America
- This role combines front-line coaching, operational excellence, executive deal strategy, and talent development
- You’ll work closely with Sales Engineering, Marketing, Customer Success, Product, and Executive Leadership to build a predictable, scalable business while helping develop the next generation of sales leaders at Iterable
- Lead, coach, and develop a high-performing team of Mid-Market Account Executives responsible for achieving and exceeding quarterly and annual revenue goals
- Drive consistent forecast accuracy through rigorous pipeline inspection, opportunity coaching, and data-driven forecasting
- Coach complex, multi-threaded sales cycles from discovery through negotiation, helping Account Executives navigate executive buying committees and competitive evaluations
- Inspect opportunities using MEDDPICC (or a comparable enterprise sales methodology) to improve qualification, execution, and win rates
- Develop consultative, Challenger-style sellers who create business value beyond product demonstrations
- Recruit, hire, onboard, and develop exceptional sales talent while fostering a culture of accountability, continuous improvement, and collaboration
- Partner cross-functionally with Marketing, Customer Success, Product, Sales Engineering, and Sales Operations to improve customer outcomes and influence go-to-market strategy
- Act as an executive sponsor on strategic opportunities, helping teams navigate complex commercial negotiations and executive relationships
- Drive operational excellence by leveraging Salesforce, Momentum, Outreach, and other sales technologies to improve productivity, inspection, and execution
- Champion the adoption of AI-powered selling tools and best practices that improve seller effectiveness and customer engagement
- Foster a culture of curiosity, ownership, and continuous learning while developing future leaders within the organization
- During your first year, you will:
- Build and develop a high-performing, engaged Mid-Market Sales team
- Deliver consistent forecast accuracy and operational rigor
- Improve rep productivity through coaching, inspection, and effective deal strategy
- Recruit and develop exceptional talent while building future sales leaders
- Drive predictable revenue growth through disciplined execution and cross-functional partnership
- Help shape the evolution of Iterable’s go-to-market strategy as we continue to scale
Our take
Iterable is a growth marketing platform that enables brands to create, execute and optimize cross-channel campaigns. The company aims to complement and support marketers in creating effective user engagement campaigns throughout the sales funnel, and across all channels.
The global omnichannel retail commerce platform market is huge, and the opportunity within this sector has bought with it considerable competition for Iterable. Despite this, the company has firmly established a name for itself and now has over 1000 customers (including DoorDash, Fender, Calm, Box, and Cars.com).
After raising significant funding in 2021, and a change in leadership that same year, Iterable has invested in several sales-focused AI technologies in order to appeal to enterprise companies. In 2025 it achieved the feat of surpassing one trillion customer interactions, demonstrating that its momentum is still very strong.
Steph
Company Specialist at Welcome to the Jungle
Insights
-3% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Jun 2021
$200m
SERIES E
Dec 2019
$60m
SERIES D
Total funding: $342.2m
Company benefits
- Medical, Dental & Vision Insurance
- Life & Disability Benefits
- Flexible Spending Accounts
- Health Savings Accounts with Employer Contributions
- Premium Calm Membership
- Health and Fitness Stipend
- Paid Parental Bonding Leave
- Paid Sabbatical
- Internet and Mobile Phone Reimbursement
- Learning and Development Stipend
- Family Forming Benefits
- Paid Holidays
- Flexible Time Off
- Balance Days
Company HQ
Financial District, San Francisco, CA
Leadership
Andrew Boni
(Founder & Chief Scientist)Was CEO of the company for 4 years. Previously an Application Services Developer at Boston College and Lead Web Developer at Kollaboration Boston.
Sam Allen
(CEO)Accomplished executive who has managed $3B+ P&Ls. Spent almost 11 years at Salesforce and previously co-founded and was CEO at ScanCafe.
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