Sales Department Lead

Silo

5d•$100,000 - $130,000•Remote

About The Position

We’re looking for a commercially-driven Sales Lead or Director of Sales to own ARR growth, lead the team, and oversee marketing—giving you the full picture from demand generation through close. You’ll work directly with the CEO, shape our GTM strategy, and play a defining role in how Silo scales. The ideal candidate brings B2B SaaS sales leadership chops and is excited to go deep in the produce and ag vertical—speaking the language of operators who live on tight margins: shrink, turns, landed cost, grower settlements, terminal market floors.

Requirements

7+ years of B2B SaaS sales experience, including meaningful sales leadership.
Proven success driving ARR growth and implementing pricing and contracting discipline.
Highly analytical—comfortable managing dashboards, forecasting, and pipeline KPIs.
Strong coaching mindset: able to elevate the performance of an existing team without tearing it down.
Experience selling platform or modular SaaS products (ERP, operations, supply chain, or vertical SaaS).
Expertise with HubSpot or a comparable CRM system.
Ability and willingness to travel to key produce markets and customer sites.

Nice To Haves

Direct experience in fresh produce, food distribution, agriculture, or supply chain operations.
Familiarity with the operational rhythms of the produce industry: seasonal buying, perishable inventory, grower relationships, terminal markets.
Experience selling into family-owned or owner-operated businesses common in produce distribution.
Knowledge of PACA, food safety regulations, or produce traceability requirements.
Existing relationships within the produce and ag community.
Bilingual (English/Spanish) preferred—the produce and ag industry is deeply bilingual, and candidates who can sell and build relationships in both languages will have a meaningful advantage.

Responsibilities

Own the full revenue engine: new logos, expansions, renewals, and pricing strategy.
Lead the migration from legacy license and NRR models toward subscription ARR.
Drive multi-year contracting and pricing discipline that supports long-term platform adoption.
Build and maintain a deep pipeline within the fresh produce and ag supply chain ecosystem.
Develop and enforce pricing guardrails that reflect the value Silo delivers in the produce vertical.
Lead a lightweight deal desk to ensure value-based selling, healthy discounting, and structured close processes.
Partner with Product and Finance on packaging, modular pricing, and ARR transformation.
Build forecasting rigor grounded in accurate CRM data and real pipeline hygiene.
Monitor KPIs, pipeline health, conversion rates, and team productivity.
Ensure disciplined, consistent CRM usage across the team in HubSpot.
Coach and elevate our existing SDRs and AEs—enhancing strengths and sharpening execution.
Provide ongoing training in discovery, objection handling, negotiation, and value selling.
Strengthen workflows, playbooks, and best practices for the full sales cycle.
Represent Silo at key industry events including IFPA (International Fresh Produce Association), Viva Fresh, and regional produce trade shows.
Build authentic relationships within the produce and ag community—distributors, growers, brokers, and packer-shippers.
Partner with Customer Success to drive renewals, upsells, and price increases with existing produce customers.
Own the relationship with Silo’s external marketing agency (Ten Acre Marketing), serving as the primary internal stakeholder directing campaigns, messaging, content, and brand strategy.
Drive product launch communications—translate new features and platform updates into compelling go-to-market messaging that resonates with produce and ag operators and converts to pipeline.
Align marketing programs tightly to the sales cycle: ensure every campaign, case study, trade show push, and content piece is designed to generate qualified leads and accelerate deals.
Coordinate launch sequencing with Product and Marketing so that new capabilities land with customers and prospects in a way that drives adoption and expansion revenue.
Build and maintain a library of sales enablement materials—one-pagers, battle cards, ROI calculators, customer stories—tailored to the produce and ag audience.
Deliver customer and prospect insights to Product to influence roadmap decisions and produce-specific feature development.
Work closely with Implementation and Customer Success to ensure smooth onboarding and strong retention for new produce customers.
Partner with Finance on ARR modeling, pricing scenarios, and revenue forecasting.