Account Executive foundations checklist

Days 1-5

Account setup

1. Enable baseline settings in Outreach to configure your instance and utilize all Outreach has to offer.

   • Sync your email so your Outreach communications come from your mailbox
   • Sync your calendar to book and hold more meetings
   • Install the Outreach Everywhere plugin to unlock Outreach functionality from your inbox
   • Enable Universal TaskFlow to execute tasks more efficiently on top of Salesforce, LinkedIn, or other websites
   • Set up Outreach Voice to make and receive dials directly through your phone or computer.
   • Configure your Kaia settings (if applicable) and enable auto-join to improve the customer experience on your customer calls and meetings
   • Configure your email signature to personalize and brand your email communications Review the Content tab in Outreach to familiarize yourself with content types your team has built to save time on customer communications

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2. Surface meaningful account data in one place with the Account Deal Grid view and create saved views to bucket similar accounts together to prospect at scale.

   • Familiarize yourself with the data-driven insights available to you in the Account Deal Grid view
   • Apply filters and customize columns based on your needs to create custom saved views. We recommend you create the following saved views:
     • Accounts assigned to you
     • Your target accounts
     • Accounts set to close this quarter
     • Upcoming renewals, expansions, or upsell opportunities

   Try it in Outreach

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3. Surface all of your opportunity data in one place with the Opportunities Deal Grid view and create saved views to improve how you review your pipeline.

   • Familiarize yourself with the opportunity data available to you in the Opportunities Deal Grid view
   • Apply filters and customize columns based on your needs, such as qualification criteria or sales methodology, to create saved views. We recommend you create the following saved views:
     • Opportunities you own
     • Deals set to close this quarter

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4. Set up Smart Account Plans for access to comprehensive account insights that you can leverage to build an effective and personalized account strategy.

   • Configure sales intelligence tiles to automatically pull in data-driven account insights (if available) to simplify account research
   • Add prospects to the Relationship Map to show the hierarchy of power within an account and call out key stakeholders, champions, and detractors

   Try it in Outreach

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Days 1-90

Prospect and manage accounts

Build a quality sales pipeline and organize your book of business.

Account planning

1. Research your accounts using Smart Account Plans to develop custom strategies that build and strengthen relationships with the right people.

   • Leverage insights from sales intelligence tiles to understand your account's business, competitors, and market position
   • Use the Engagement Timeline's concise summary and timeline of account activities to identify key takeaways and next steps
   • Ask Smart Account Assist questions for instant account insights you can use to pinpoint risk and opportunity
   • Use the Relationship Map to understand lines of power and entry points into your account so you can target qualified buyers and champions
   • Outline relevant findings in Strategic Initiatives and Outcomes to share comprehensive insight into your account
   • Outline your prospecting plan in Engagement Strategy to develop a targeted account engagement strategy
   • Add or review any competitive contract end dates in the Purchases tab

   Try it in Outreach

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Prospecting

1. Increase target account penetration to generate more pipeline by reaching out with the right message to the right prospect at the right time.

   • Hover over the following insights on the Accounts page to understand account engagement:
     • Sequences: Are there enough prospects actively in sequence within your account?
     • Emails: Is your account actively being engaged over email?
     • Status: Do I have any upcoming Meetings or Tasks? What is the Deal Health Score of the opportunity?
     • Last contact date: Has this account been engaged recently?
   • When you identify an account that needs attention, easily identify and sequence qualified buyers using Persona filters
   • Edit and personalize your sequence to optimize response rates

   BEST PRACTICE:

   To increase conversion rates and account penetration, Outreach recommends that each of your target accounts has at least five prospects actively in sequence, with two prospects being priority personas. Use research from your account planning in Smart Account Plans above to tailor sequences to your prospect or account.

   Try it in Outreach

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2. Automate busywork when executing tasks in Outreach 360 so you can focus on the strategic selling efforts and personal touches that increase qualified pipeline.

   • Review your upcoming tasks to understand your task load for the week
   • Sort and group tasks to increase productivity by prioritizing how you spend your time
   • Log and complete LinkedIn tasks and use Universal Taskflow insights to personalize engagements
   • Log and complete Email tasks and use Smart Email Assist to generate emails using AI in just a few clicks
   • Log and complete Call tasks to make dials directly in Outreach Voice. Handle objections in real-time using Kaia's content cards, created by your Outreach Admin.
   • Generate a calendar invite in one click while on the call and ask your Outreach Admin to set up automated meeting reminders to reduce cancellation and no show rates
   • Enable desktop notifications for inbound leads so you can immediately take action regardless of what webpage you're on

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3. Save time when communicating with customers using Outreach's integrated email experience to access content directly in your inbox.

   • Use Sequences to schedule an automated follow-up to keep customers engaged and ensure threads stay active
   • Use an email bump to get a reminder when a customer hasn't responded
   • Use Templates and Snippets to insert pre-written content in just two clicks
   • Use Smart Email Assist to generate emails in under a minute using AI
   • Use Meetings to insert your meeting availability so customers can automatically book time on your calendar

   Try it in Outreach

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4. Align your prospecting targets with earnings goal and see which activities you need to complete to hit quota using the Pipeline Generation calculator.

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60 days to complete

Manage and guide deals

Align with your buyers with confidence.

Meeting management

1. Schedule and host meetings and calls in Outreach to increase credibility with customers and advance more deals to the next stage.

   • Schedule a meeting using auto-populated meeting types to capture important details
   • Prepare for the meeting by reviewing the Smart Account Plan and Success Plan associated with your opportunity
   • Invite Kaia to join your meetings so you can be more productive on calls
   • Use Kaia's AI-generated real-time content cards, created by your Outreach Admin, to handle objections
   • Gauge customer engagement and course correct in real-time with Kaia's real-time call analytics

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2. Follow-up with prospects using Kaia and Smart Call and Meeting Assist to avoid deal delays.

   • Review auto-generated summaries for action items, key talking points, and next steps for each meeting
   • Ask Assist questions for detailed insight and deep links on what was discussed during the meeting
   • Use Assist to send a highly tailored follow-up with clear, specific, and actionable next steps in just one click

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Deal progression

1. Improve win rates by creating mutual action plans to scope and align on purchase criteria with buyers.

   • Use Sequences to schedule an automated follow-up to keep customers engaged and ensure threads stay active
   • Use an email bump to get a reminder when a customer hasn't responded
   • Use Templates and Snippets to insert pre-written content in just two clicks
   • Use Smart Email Assist to generate emails in under a minute using AI
   • Use Meetings to insert your meeting availability so customers can automatically book time on your calendar

   Try it in Outreach

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2. Maintain deal momentum and multi-thread by using Success Plans to collaborate with buyers and align on success indicators.

   Use your Success Plan's Timeline to track and understand the steps and time required to reaching specific milestones within the deal cycle:

   • Break the sales process into steps using Phases
   • Within each Phase create Events to capture project milestones and use Details and Subtasks to outline requirements to reaching a successful outcome
   • Assign Owners and Followers in Events to give prospects and internal teammates visibility into milestones
   • Meet with your champion to walk through your sales process and gather insights for your Success Plan including success metrics, business objectives, required features, and stakeholders
   • Add any additional milestones from your buyers side as Phases or Events

   Try it in Outreach

   Use Success Criteria to map customer value and drive alignment:

   • Use Sections to add the success metrics and business objectives your champion shared
   • Use Details within Sections to outline the value your product brings or specific capabilities

   • Use Teams to share the Success Plan with relevant stakeholders
   • Interact with buyers using Phases, Tasks, and Comments on the Timeline
   • Reference your Success Plan on every customer call to track progress and adjust or capture new Success Criteria
   • Set up notifications to be alerted when internal or external stakeholders make changes to your plan
   • Add Resources to centralize information so that all parties in your buying committee have access to the information they need
   • As new stakeholders enter the buying process, review the Timeline to share progress so far and share Success Criteria to align on value

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Opportunity Mananagement

1. Improve visibility and identify potential risk to your pipeline in the Opportunity Deal Grid.

   • Update the Opportunity Deal Grid to keep leadership updated in real-time by making edits to your opportunities Close Date, Amount, Qualification Criteria, Next Steps, and Stage
   • Use Deal Health to identify and take the best course of action and proactively decrease pipeline risk
   • Escalate risk by creating tasks for your manager or leadership to review and address

   Try it in Outreach

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2. Review your progress on an opportunity with your sales manager to spot risk and strategize on next steps using insights from the Opportunities overview page.

   • Review key opportunity stats such as Amount and Close Date for a clear view of where the deal is at
   • Review the Engagement Timeline to track the entire history of your opportunity; every email, call, or meeting that's occurred between your buyer and teammates
   • Spot risk early with Health Insights and use Where to Focus and Suggested Actions to create tasks or sequences to get deals back on track
   • Review previous calls and meetings using Kaia features like the Transcript and Analytics to pinpoint specific customer concerns and insights
   • Review your Plan to align on the path to close and reduce late stage risk in opportunities

   Try it in Outreach

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60 days to complete

Resources for your first 90 days in Outreach

Use these resources to learn more about how to use Outreach to prospect and manage your accounts.

1. Strategy articles and videos

   • How to manage accounts strategically in Outreach
   • Master email prospecting: Templates, examples, and more
   • How Outreach makes your inbox work for you
   • 11 account planning best practice to win more business
   • Four reasons why Outreach reps can't live without Kaia
   • How AEs use AI to follow up with prospects 
   • How to improve win rates by 26% with best-in-class mutual action plans
   • How an AE uses Outreach
   • How an enterprise AE manages her book of business in Outreach

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2. University courses and Office Hours

   • AE Office Hours
   • AE sequences for deeper engagement
   • Leverage Outreach from your inbox for AEs
   • Task management for AEs
   • Meetings for AEs
   • Improve deal execution with Success Plans
   • How to use Kaia: Kaia for Outreach users

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60 days to complete

Retain and expand

Grow expansion revenue and reduce churn.

1. Use Outreach to secure renewals and expand contracts beyond the initial land.

   • Maintain regular touchpoints with key stakeholders to improve retention within your accounts
   • Use the Prospect Relationship Map to target qualified champions and buyers for expansion opportunities
   • Use the Kaia Topics Reports to view trends in your conversations, whether they are MEDDPIC topics, custom topics set up by your Outreach Admin or any of the standard AI-powered topics available out of the box.
   • Use Success Plans to help facilitate a seamless account handoff post-sales cycle and continue collaborating with customers and your internal team by using Success Plans for expansion opportunities.
   • Use the Opportunities page to identify and escalate risk during 1:1s to save renewals or expansion deals
   • Track your account's purchases and relevant data to identify retention and expansion opportunities and run coordinated plays to increase the lifetime value of your account

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Performance management

Data-backed performance insights to help you create and close more pipeline.

1. Track and improve your progress towards your activity KPIs using the Pipeline Generation Report.

   • Review your meeting conversion rate, we recommend aiming for a conversion rate of about 10% to ensure you hit your meeting booked rate. To improve your meeting conversion rate, make sure that you're targeting higher level personas with personalized sequences.
   • Look at your meetings held rate, we recommend aiming for a rate of about 70% to ensure you hit your meetings target. To improve your meetings held rate, make sure that your message to prospects is driving urgency and interest.
   • Compare your cumulative calls to the Calls metric from the calculator, are you conducting enough calls?
   • Review your call connect rate, we recommend aiming for a CCR of about 10%. To improve your call connect rate, consider adjusting when you call prospects and ensure that before you call prospects you have done your research to drive urgency and interest.

   Try it in Outreach

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2. Track activity and meetings metrics in the Team Performance Report to improve conversion rates.

   TIP:

   When prospecting, you should be targeting at least two priority personas for each of your target accounts and using persona-based, personalized sequences to improve conversion rates.

   • See how you're pacing to your monthly goals identified with the Pipeline Generation Report above
   • Review the seniority levels of the prospects you're contacting and ensure that you're engaging decision makers who are most likely to book meetings with you
   • Review the sequences that you're using to ensure that your putting the right level of effort into prospecting with personalized messaging
   • Review your team's top performers to see their mix of leadership levels and how they execute personalization and messaging and apply learnings accordingly to replicate their success

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3. Book more meetings using insights from the Sequence Performance Report.

   • See which sequences your team is using to book the most meetings. Are there sequences you can be using to see similar results?
   • Sort by positive email sentiment to see which sequences receive the most positive responses. Are there sequences you can be using to see similar results?

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