Summary
Overview
Work History
Education
Skills
Timeline
Accomplishments
Hi, I’m

Amanda Sylvester

Portsmouth,NH

Summary

Experienced investor relations and business development professional with expertise in supporting capital raise initiatives, managing institutional investor relationships, and leading the development of investor and marketing materials. Trusted for crafting investment pitch decks, CIMs, co-investment summaries, newsletters, and transaction communications. Skilled in conducting effective investor outreach, managing CRM systems, sourcing prospective investors, and delivering a top-notch investor experience. Demonstrated success collaborating directly with founders and senior leadership in fast-paced, entrepreneurial environments.

Overview

7
years of professional experience

Work History

Highland Advisory Group LLC

Director, Investor Relations & Operations | Founding Team Member
03.2024 - Current

Job overview

  • Partnered with firm Founder to launch and build a boutique M&A advisory firm, establishing core infrastructure across investor relations, business development, and operations.
  • Lead investor engagement efforts supporting private equity firms, family offices, and strategic investors.
  • Manage full investor lifecycle: sourcing, outreach, conveying firm strategy, pitching, relationship tracking, and closing support.
  • Create all investor-facing materials, including confidential information memoranda (CIMs), deal pitchbooks, co-investment summaries, and monthly updates.
  • Oversee CRM strategy and management, maintaining a pipeline of 20,000+ contacts and ensuring real-time data accuracy and engagement tracking.
  • Conduct investor research, lead generation, and segmentation to build targeted outreach campaigns.
  • Uphold rigorous quality standards in communications and deliverables, ensuring a tier-one client and investor experience.

Willie’s Superbrew

Director of Sales Operations
06.2023 - 03.2024

Job overview

  • Reported to CEO as part of executive leadership team; developed operational systems for distributor management, inventory forecasting, and production planning.
  • Led data-driven sales operations initiatives to support company growth, new product launches, and brand activation strategies.
  • Streamlined reporting processes, improving operational visibility and forecasting accuracy across markets.

Downing Capital Group

Portfolio Operations Director
09.2021 - 06.2023

Job overview

  • Built and scaled operational infrastructure across multiple early-stage portfolio companies, driving operational readiness for growth and investor engagement.
  • Established strategic vendor partnerships and implemented standardized systems to support scalability.
  • Authored the “Operations Canon,” a foundational playbook adopted across portfolio companies.

Bigelow LLC

Associate, Client Services
12.2017 - 09.2021

Job overview

  • Supported M&A advisory transactions for private business owners across all phases from engagement to close.
  • Created all marketing, investor-facing, and diligence materials, including company websites, videos, and pitch decks.
  • Led CRM system overhaul, significantly improving data quality, investor tracking, and reporting efficiency.
  • Partnered with senior leadership to coordinate investor communications and prepare clients for market processes.

Education

Stony Brook University
New York

Bachelor of Science

University Overview

Skills

  • Relationship building
  • Strategic planning
  • Verbal and written communication
  • Decision-making
  • Creativity and innovation
  • Project management
  • Story pitching
  • Investor relations
  • Problem-solving
  • Powerpoint presentations
  • Willing to learn

Timeline

Director, Investor Relations & Operations | Founding Team Member
Highland Advisory Group LLC
03.2024 - Current
Director of Sales Operations
Willie’s Superbrew
06.2023 - 03.2024
Portfolio Operations Director
Downing Capital Group
09.2021 - 06.2023
Associate, Client Services
Bigelow LLC
12.2017 - 09.2021
Stony Brook University
Bachelor of Science

Accomplishments

Accomplishments
  • Contributed to the launch and growth of a boutique M&A advisory firm, helping build the investor relations and operations infrastructure from the ground up.
  • Primary lead for creating investor and marketing materials supporting multiple successful client transactions and capital raise initiatives.
  • Led CRM platform overhauls and data management initiatives across two firms, supporting investor pipelines ranging from 20,000 to over 200,000 contacts.

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Amanda Sylvester