Jessica Rasheed

Global AI-Native Sales, Customer Acquisition & Demand Generation | Brand Growth Expert

San Diego, California, United States

About

I am a Sales and Demand Generation professional with 10+ years of experience creating enterprise-level pipeline engines, streamlining operations and processes in B2B SaaS. I work with CRO's and VP's of Sales to set up and improve their demand generation and top of funnel process: - I offer prospecting training in B2B SaaS - Discovery and training for ICP and Persona relevant to your team (Built 3x Playbooks from scratch) - Lead Journey: I've implemented lead qualification and scoring frameworks across several orgs - Set up KPI's and metrics for SDR teams to boost performance and generate high-quality pipeline - Address attribution points in your lead and customer journey to increase conversions cross the funnel If you're keen to address any of the above, send me a message to book a free intro call! • Growing and scaling a global SDR team from 5 to 40+, including front line SDR management at Retail, Payments, Fintech, EdTech company as a Director of Global Sales Development (direct reports of 5 SDR managers) • Building and scaling personalized outbound strategy for SDR’s and Account Executives, as well as increasing alignment between Sales and Marketing • Sourcing new business at the top of the funnel (+$600M quarterly pipeline) and driving Sales Executives to closed won revenue for SMB and MMK segments • Implementing and administering CRM for reporting and analytics - Salesforce Admin 201 • Familiar and capable of operating GTM Tools: Salesforce CRM & PRM, Outreach, Gong.io, LeadIQ, ZoomInfo, Clearbit, LinkedIn Sales Navigator, Asana, Tableau, Google Analytics, Orum • International experience in the Middle East, Southeast Asia & Europe. Currently based between San Diego, CA, USA and Sydney, Australia

Experience

  • GTM AI Transformation Consultant - Outbound & Inside Sales at Freelance
    Sep 2023 - Present · 2 yrs 11 mos

    Clients include portfolio companies of Insight Partners (B2B / B2C Series A - C) Core Services: Designing and deploying AI-enabled workflows for qualification, enrichment and routing, including AI native models for forecasting and manager training SDR System Playbook Design for Outbound & Inbound (org design, cadences, talk tracks, KPIs) SDR & Funnel Audit (CVR diagnostics + 90-day roadmap) Demand generation & Marketing programs leveraging Agentic AI for Inbound Qualification (trigger and account based targeting for MQL's) Fractional RevOps Advisory (marketing–sales alignment). Marketo Certification (2021), Outreach Certification (2022), Trained in Winning by Design

  • Founder & CEO at Jove
    Feb 2026 - Present · 6 mos

    Jove is the first social app designed to connect people for local sports and outdoor activities like cycling, run clubs, ski trips, pickelball, volleyball, golf and wellness events. Our mission is to get you outside more often and with more ease, through AI-enabled event planning, whether you're an individual or a business looking to manage events and grow your local in-person communities. @joveoutdoors

  • Director, Global Pipeline Generation & SMB Inside Sales - Square at Square
    Nov 2024 - Apr 2026 · 1 yr 6 mos

    Leading Square's global pipeline generation + SMB inside sales team in North America, Australia, UK, Europe and Japan to focus on new business generation alongside Brand Marketing & Partnership, building Sales playbooks (outbound & inbound) for Marketing and Channel Sales, and overall top-of-funnel strategy for Square Sales. Led the close and SDR-assisted onboarding of SMB Square sellers. Team includes: 4 global managers, and 36 SDR's + 20 offshore SDR's + 2 BPO Team Leads. Achievements: - Created Custom GPT's and applied Agentic AI to transform Lead Scoring, Routing, Management coaching and call reviews, increasing SDR productivity by 35% and simultaneously increasing the promotion rate to AE / AM roles - Built full-funnel playbooks across Product, Marketing, Channel/ Partnerships leads and introduced revamped performance management + QA framework for SDR's and off-shore vendors (BPO) - Led AI tranformation and adoption across Inbound & Outbound teams, including AI-led qualification and routing - Led the execution of the first 'cold' lead generation program alongside Marketing, introducing Affiliate Partners and Paid Lead gen programs globally. Contributed to 30% of Square's quarterly net revenue through this joint SDR & Marketing program - Exceeded quarterly pipeline and SAL targets (Q4 25: 113%, Q3 25: 107%, Q2 25: 121%) - Managed all GTM cross-functional initiatives with Marketing, Partnerships, RevOps and Channel Sales, which led to an increase in MQL conversion by 12% for Marketing and 18% for Channel/ PQL's - Promoted 14 reps from SDR to AE, 2 to Account Management - Led first-ever pipeline based Global Sales Development reporting and KPI revamp that increased SDR productivity by 25% within 4 months - Created and executed an SMB Inside Sales strategy leading to $13M in annual processing value - Created Custom GPT's for Sales Coaching, and used Square's LLM's (Goose and G2) to build Forecasting and pipeline management - improving weekly conversion rates

  • Preply (2 yrs 2 mos)
    • Director of B2B Global Business Development & SMB Inside Sales
      Dec 2021 - Nov 2023 · 2 yrs

      (Managing 5 SDR Managers/ Regional Leads globally) Leading the growing Global new business Business Development team, growing from 5 to 40+ SDR's & regional Team Leads located in EMEA, LATAM & North America amidst Series C funding. Led SDR-assisted full-cycle close and onboarding for SMB. • Built 2nd line leadership role across Preply’s global sales function to close new business deals across EMEA and North America - 5 SDR Managers across US and Europe as Direct Reports • Reporting to VP of Sales; scaled org from 5 reps to 35 reps and 5 regional leads selling to HR, Benefits, Wellness, Payroll • Created the Preply B2B Demand Gen program alongside Marketing by introducing Paid Social & B2B Product Campaigns, sourcing $800K in MQL's per quarter • Own Sales outreach and account penetration strategies, including top of funnel forecasting and metrics • Q2 2022: 91% (impact due to war) , Q3 2022: 123%, Q4 2022: 95%

    • Manager, Global Outbound Pipeline Generation & Market Expansion
      Oct 2021 - Dec 2021 · 3 mos

      Leading the North America and EMEA SDR team (inbound and outbound); scaled SDR team from 5 in Barcelona, Spain to 35+ globally across 10+ markets, including promoting and hiring team leads and managers across the function. SDR Ops Lead for all global markets (sales engagement optimization, partnership with marketing and lead gen to increase lead volume and top of funnel CVR) • Q4 2021: 85%, Q1 2022: 111% • Increased outbound meetings booked by 25% (SQL's), generating 2x in pipeline for AE team than previously

  • Manager, Outbound Sales & Sales Operations at Tubular Labs
    Nov 2020 - Nov 2021 · 1 yr 1 mo

    - Created the first Social Paid Media initiative via an Account Based Marketing Meta Ads program alongside CRO to generate ENT leads - Created and executed the global Account Executive and Sales Development Outbound Sales Program, with responsibilities in Sales Operations and Enablement: • Q3 2020: 87%, Q4 2020: 103%, Q1 2021: 111%, Q2 2021: 91% (attrition), Q3 2021: 95% • Managed pipeline, deals and forecasts of 3 SMB New Business AE's, including Expansions