Open to opportunities

Ben Cruikshank

@bencruikshank

Sales Development Manager and AE who builds outbound systems that turn targeted prospecting into quota-winning pipeline.

United States

Message

What I'm looking for

I’m looking for a GTM leadership role where I can build and improve outbound and SDR/AE execution—using sharper ICP targeting, messaging, coaching, and measurable pipeline outcomes to create predictable, scalable growth.

I’m a Sales Development Manager and Account Executive with 8+ years across SaaS, HR tech, and health tech—partnering strategy with operational execution to build outbound motions that perform. As a 3x founding Sales Development Manager, I’ve led teams through new-program launches, rebuilt targeting and messaging, and coached reps to stronger results.

Most recently, I moved into the Health Plans business as an Associate Account Executive after serving as a Sr. Strategic Sales Associate. I’ve delivered 175% of Q3 quota and 100% of Q4 quota, supporting complex health plan sales cycles with stakeholder strategy, positioning, and deal execution across clinical, product, and commercial buyers.

Across my founding and leadership roles, I’ve driven measurable performance improvements by rebuilding outbound strategy and tightening ICP discipline. At Beamery, I led 4 SDR teams across 3 countries and improved performance from 60% of goal to consistent 100%+ attainment, while increasing email open rates by 50%, response rates by 30%, and cold call conversion rates by 50%. At Color, I built the company’s first outbound sales development motion and created more than $2M in pipeline for a net-new product, and I trained enterprise AEs on outbound strategy and prospecting best practices. At Kaia Health (now Sword Health), I generated more than $5M in pipeline by building core SDR infrastructure and leading outreach across multiple verticals.

Earlier in my career, I helped scale multi-channel SDR and ABM programs to drive pipeline velocity and deal size, including leading the SDR function through 14 consecutive months of month-over-month growth and earning rapid promotions and awards. I also bring operator mindset from modernizing a multi-property portfolio by digitizing operations, budgeting, and financial controls—so I’m always looking for practical systems that make growth repeatable.

Experience

Work history, roles, and key accomplishments

Current

Associate Account Executive

Current

Carrot

Sep 2025 - Present (7 months)

Delivered 175% of Q3 quota and 100% of Q4 quota as an Associate Account Executive in the Health Plans business. Supported complex health plan sales cycles with stakeholder strategy, positioning, and deal execution across clinical, product, and commercial buyers.

Health Plan Sales Account Executive Quota Management Positioning Deal Execution Cross Functional Collaboration Pipeline Generation Revenue Growth

Current

General Manager

Current

Cruikshank Investments

Jan 2021 - Present (5 years 3 months)

Modernized a multi-property portfolio by digitizing operations, building budgets, and establishing financial controls as General Manager. Improved operational and financial execution through updated processes and governance.

Digital Operations Budgeting Financial Control Business Process Improvement Governance

Global Sales Development Manager

Beamery

Jan 2022 - Jan 2023 (1 year)

Led 4 SDR teams across 3 countries, improving performance from 60% of goal to consistent 100%+ attainment for the first time in program history. Rebuilt outbound strategy to improve pipeline quality and conversion, increasing email open rates by 50%, response rates by 30%, and cold call conversion rates by 50%.

SDR Leadership Outbound Strategy Targeting Messaging Lead Qualification ICP Discipline Cold Calling Pipeline Conversion Sales Coaching

Senior Sales Development Manager

Color

Jan 2021 - Jan 2022 (1 year)

Built the company’s first outbound sales development motion, shifting the team from fully inbound to hybrid pipeline generation. Created more than $2M in pipeline for a net-new product and trained enterprise AEs on outbound strategy and prospecting best practices.

Outbound Sales Development Pipeline Generation Pipeline Strategy Sales Enablement Sales Prospecting Sales Training Lead Qualification Messaging

Manager, Enterprise Sales Development

Limeade

Jan 2020 - Jan 2021 (1 year)

Led the SDR function through 14 consecutive months of month-over-month growth and improved pipeline velocity and deal size through multi-channel ABM and SDR programs. Partnered with sales and marketing leadership to align enterprise account strategy.

SDR Leadership Multi channel Marketing Account Strategy Sales Alignment KPI Tracking Revenue Operations

Enterprise SDR

Limeade

Jan 2018 - Jan 2020 (2 years)

Supported enterprise growth by executing multi-channel ABM and SDR programs that increased pipeline velocity and deal size. Earned promotions within under 3 years and was recognized with the Founder’s Award and President’s Club.

ABM Lead Qualification Pipeline Building Quota Attainment CRM Hygiene KPI Tracking Sales Messaging

SMB Account Executive

DataSphere

Jan 2017 - Jan 2018 (1 year)

Promoted in 5 months after averaging 155% quota attainment as an SMB Account Executive / Sr. SMB Account Executive.

SMB Sales Account Executive Quota Attainment Pipeline Building Outbound Prospecting KPI Tracking Sales Forecasting Customer Acquisition

SMB Account Executive

Yext

Jan 2016 - Jan 2017 (1 year)

Achieved 110% quota attainment over 13 months as an SMB Account Executive.

SMB Sales Account Executive Quota Attainment Outbound Prospecting Lead Qualification Pipeline Generation Sales Messaging KPI Tracking Customer Acquisition

Founding Sales Development Manager

Kaia Health

Jan 2021 - Present (5 years 3 months)

Built the core SDR infrastructure, including hiring profile, onboarding, compensation design, and lead routing. Generated more than $5M in pipeline by leading outreach across Enterprise, Mid-Market, SMB, Public Sector, and Health Plans.

SDR Hiring Profile Design Onboarding Lead Routing Mid Market Outreach Pipeline Generation