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Justin Michael and Tony Hughes: Tech-Powered Sales

Selling with technology

Selling is leadership, plain and simple. It demands the masterful ability to positively influence others and it must be done with integrity. Without sales success, there is no company success.

Justin was handpicked by Ben Sardella, cofounder of Datanyze, and Bryan Franklin, CEO of OutboundWorks, to work on an ambitious stealth project seeking to fully automate the SDR function by building an AI model of his brain. The result was hundreds of concurrent Outreach, SalesLoft and Reply.io cadences generating over one million emails.

The things that make us truly human are soul, real empathy, relationships, curiosity, values, intellect — and the effective use of tools, no matter the level of sophistication.

“The future of B2B value selling is when buyer sentiment meets seller relevance with human engagement empowered by technology.” — Tony Hughes

According to a 2020 survey by Revenue Collective covering more than three thousand inside salespeople and companies generating more than $ 26 billion in revenue, 83 percent of inside sales reps fail to hit the target and almost 40 percent last less than six months in their role.

Having made significant inroads into retail sales, the bots are now coming for B2B sellers. If all you do is provide information and help someone transact, you’re in trouble: they want a purchasing platform and an algorithm, not a salesperson and pressure.

The brutal reality is that employees, workers and staff are regarded as units of production. Clients, customers, and consumers are regarded as units of consumption. Economists use the term zero marginal product (ZMP) to describe when someone adds no value at all.

Do you think you’re safe in sales because you build relationships? Really? In a profession where the majority already fail . . . is that realistic? Self-delusion is not an antidote; hope is not a strategy.

For the first time in history, capital applied to technology can fully replace expensive and high-overhead humans.

Tradespeople must become artisans; knowledge workers must become insight professionals; leaders must become navigators of ambiguity and disruption.

The Harvard Business Review defines technology quotient as: Our ability to assimilate or adapt to technology changes by developing and employing strategies to successfully include technology in our work and life. Someone without TQ today is a dinosaur on the brink of extinction.

Are you leveraging Tray.io, Zapier, Workato, Automate.io or Syncari to splice tech stacks together via application programming interfaces (APIs)?

Are you using 80 percent of your time selling versus the average of 36 percent?

Part I: Sales-borg Theory

Execution is where most things fail. It’s not the knowledge that will change your life, it’s the doing that makes all the difference.

Technology is best at dealing with huge amounts of data, sifting for signals amidst the noise by pattern matching or identifying trigger events, automating repetitive processes or tasks, doing “what-if” analyses, making recommendations and even rudimentary personalization at scale. Humans, on the other hand, have genuine empathy and can transfer belief and build trust with a real human connection through relevant storytelling. Machines think and do. Humans feel and engage. A cyborg-like fusion of both sides is needed for sales success today and into the future for productivity and effectiveness.

If you are an operations person, try to make sure everything is syncing perfectly all the time. Have your sales engagement tool matching your marketing automation processes, and make sure that your revenue strategy reflects throughout your whole funnel. This is where sales or revenue operations professionals will become orchestrators of the bots, making the tech stack truly sing.

These super-sellers embrace “Smarketing” mapping the entire customer journey across inbound and outbound touchpoints, harnessing the power of intelligent platforms and automation to inject truly human engagement at exactly the right times. Smarketing is a trademarked term coined by Peter Strohkorb, an amalgam of sales and marketing.

From Human to Superhuman

The trends in the 2020s are conspiring against everyone in sales by reducing attention spans, increasing resistance to change and hardening the status quo.

Real sellers create opportunities rather than just manage the leads handed to them.

For many leaders, the sales function is an expensive black box that generates inconsistent results. Fixing this problem is a Holy Grail of business that we’ve been immersed in for decades.

The sales engagement platforms (SEPs) have reduced a significant amount of the fragmentation, but the ecosystem of tools is still disparate and they don’t talk to each other. SEPs are the next CRM, but they don’t always play well with others.

In a world where there are no bidirectional APIs for what is truly needed to thrive in modern selling, you must become the human middleware bringing everything together.

The awful truth is that most sellers do very little selling at all. They confuse thinking about selling, planning their selling, preparing and researching for selling, talking about their selling . . . with actual selling!

Aaron Janmohamed, Global Product Marketing at XANT, writes: “With the remaining 30 percent of their time supposedly spent on selling, how much of that is actually targeted on the right sales activities? Reps spend 297 percent more time on deals that will never close vs. deals that will.

In 2010, it took 4.7 attempts to secure engagement with a prospect. Fast-forward to 2018, and it was 9.1 attempts.

An inside sales rep (ISR) is mainly known as an SDR (sales development rep) for inbound and a BDR (business development rep) for outbound. An inside sales role is sometimes called MDR (market development rep) or MRR (marketing response rep) or LDR (lead development rep) or ADR (account development rep). In large companies, these roles are often supported by SDAs (sales data analysts). The main distinction between ISR roles is whether they are focused on qualifying inbound inquiries or marketing leads, versus driving outbound activity to create qualified leads that are given to more senior salespeople in the field. Inbound reps sometimes report to marketing because they are qualifying the marketing department’s leads to move them from MQLs to SQLs. Outbound reps usually report to sales because they feed the field reps (AEs) with qualified leads.

Essentially what will need to be created is some middleware GUI Minority Report dashboard that plugs into all the platforms via API. For now, we have Tray.io and Zaps to build that glue, or SDR analysts, or VAs behind a Mechanical Turk.

“You never change things by fighting against the existing reality. To change something, build a new model that makes the old model obsolete.” — Bucky Fuller[1]

Venture capitalist Tomasz Tunguz of Redpoint Ventures provides the best exhortation we’ve found for reimagining how artificial intelligence can truly transform and enable sales. So, engineers, entrepreneurs and product folks reading here, please go build this: The startup that disrupts Salesforce will be worth much, much more because instead of simply recording leads and sales, the next CRM will create business for its customers leveraging social proof. It won’t be enough for a CRM to inform a salesperson which potential customer to call the way Salesforce’s task list operates today. This new CRM will scour the web to find potential customers, discover points of social proof with potential customers increasing close rates and finally record the transactions in the system.

Everything else being equal, technology is a mind-blowing game changer and you need TQ to play and win!

What’s Your Technology Quotient?

If you don’t have the essential stack nailed, you are underinvesting in your team and already being lapped by competitors.

The average high-growth startup is spending $ 1,000 per rep, per month.

  • CRM/CX/Marketing Automation. Salesforce, Microsoft Dynamics, Hubspot.
  • Social/Networked Intelligence. LinkedIn Sales Navigator (Navigator or Nav), Twitter, YouTube, even Strava.
  • Sales engagement platforms (SEPs) . These are also called sequencers, cadences, flows or plays. Outreach, SalesLoft, RingDNA, Revenue Grid, Outplay, Groove, XANT, Apollo.ai, FrontSpin, MixMax, AmpleMarket, PersistIQ, lemlist, Autoklose, Airborne, SFDC HVS, HubSpot, Marketo Connect, Pardot, ZoomInfo (Tellwise).
  • Data enrichment. Cognism, ZoomInfo/Discover.org, Adapt.io, SalesIntel.io, LeadIQ, Seamless.ai, Lusha, Triggr, RocketReach, Infotelligent, ClearBit, Outboundsales.io, CloudLead.co, UpLead, LeadGenius, Modigie, VA’s. Custom Built scrapers for event apps such as Slack, and so on.
  • Trigger event monitoring. ZoomInfo “Scoops”, InsideView, Navigator, Triggr.ai, Engagio/DemandBase, and so on.
  • Parallel Assisted Dialers (PADS). This technology dials thousands of numbers then hot-switches a live caller while screen-popping the data you need for the conversation. ConnectAndSell, ConnectLeader, Orum. Dialers. RingDNA, Aircall, Dialpad, Truly, RingCentral, ZoomPhone — dial right from the CRM, automate text (SMS), leave prerecorded voicemail drops, and capture call records in CRM.
  • Collaboration. Remote digital meetings. Zoom.us, Teams, Google Meet, and so on.

Advanced Stack Additions

  • Intent data. Bombora, TechTarget, Slintel and 6sense.
  • Firmographics, psychographics and technographics. Orb Intelligence (D&B) for deeper info on businesses including growth and acquisition, HG Insights (formerly HG Data), Triggr.ai for tech stack intel (i.e., technographics).
  • Rep persona and brand management. Buffer, LinkedIn, Hootsuite, SocialBee, Lately.ai (AI for social media management).
  • Front site chatbot. Drift, Conversica.
  • Prospect enrichment and ML-driven personalization suggestions. Nova.ai, Autobound.ai. Research curation. CheetahIQ, GR8 Insight, and so on.
  • Communication and DM videos. Drift, Vidyard, Bombbomb, LinkedIn. Calendering.X.ai, Calendly, Chili Piper, Kronologic.
  • Better conversations and on – brand messaging. Grammarly, Lavender, and so on.
  • Email management 2.0  Superhuman, Hey (Basecamp), Front, and so on.
  • Smart teleprompter and conversation intelligence. Gong.io, Chorus.ai, ExecVision, RingDNA, Jiminny, Wingman, Fireflies.ai.
  • Real-time call and voice guidance. Balto, VoiceVibes, Quantified Communications, Verbal Transactions, Beyond Verbal.
  • Presentation and demo Performance. mmhmm, LivePreso, Open Broadcaster Software (OBS).
  • Content automation. Descript, Remastermedia, SocialBee.
  • Reply management/sentiment analysis. LeadGnome, Outreach.io.
  • Affiliate referral automation. CoSell.io.
  • Account mapping and planning. Lucidchart (allows reps do strategic prospecting and territory planning visually), Airtable, Trello.
  • Forecasting. Clari, Ebsta, Boostup.ai, InsightSquared, AtriumHQ, Einstein within Salesforce.
  • Deal management. Dealpoint.io, Dooly, Slack/Troops deal rooms, P6 Risk, Slack/Einstein within Salesforce.
  • Proposal contract management. Docusign, Adobe eSign, CPQ.
  • Win/Loss insights. Trinity Perspectives.
  • Live crowdsource intelligence. Guru, Tribyl.

Salesforce, with high velocity sales (HVS), is accelerating their leadership by moving deeper into the sales engagement arena. Everybody is getting into the game of proactive outbound sales — as this is where the battle for survival and dominance is fought, especially in tough economic times.

You must have a single source of truth about the prospect journey and customer life cycle. This platform must bring marketing, sales, professional services and support together for a truly customer-centric view of revenue operations (rev-ops).

CRM such as Salesforce, plus sales engagement such as Outreach or salesLoft, plus sales intelligence tools such as LinkedIn Sales Navigator and ZoomInfo are essential.

Beyond being competent and committed to CRM, sellers need a meta framework to utilize all the sales tooling: marketing automation, BI, sales intelligence, social, triggers, calls, emails, InMails and programmatic campaigns.

The Rise of the Machines

Without the Drift-bot style technology, the average conversion rate on a landing page is 2.3 percent.

But how about filling that site with rich inbounds based on your SalesLoft outbound activity? Google Duplex, an outbound AI that calls people on the phone and has conversations.

The future of sales automation is perpetual cycles of outbound that generates inbound that generates engagement that results in customer acquisition.

The future of buying and selling may actually go full-blown AI on both sides of the aisle where the top funnel is gone and it’s just bots moving at the speed of high frequency trading via blockchain in the cloud. . .

The big four in the arena of sales engagement platforms (SEPs) are currently: XANT, SalesLoft, Groove and Outreach; and the category will continue to proliferate before consolidating.

Check out Everstring: The company’s predictive analytics platform helps companies identify and engage with their best customer prospects.

The real goal of all sequences, cadences, flows and plays is to think about the Turing test. Readability experiments using the Flesch-Kincaid scoring method, which is basically a proxy of complexity of the text. Like Grammarly on steroids, Lavender tells you how succinct and effective your writing is while you write!

Personalization. Another example of how advanced things are is OpenAI’s GPT – 3 “language generator”.

We’re coming back to technology quotient (TQ) here because it is the game changer. It is the meta-skill that unlocks sales excellence and the flywheel effect.

Work ethic has always mattered, but the best operators know to work hard and smart. TQ is the new smart and hard because the technology does most of the work.

The future of selling is not about SDRs trying to piece together all the necessary components of a tedious process, but rather about everyone (sales, marketing, operations and leadership) growing the pipeline by optimizing scalability of their processes to reach their target personas. This is what will lead to a sustained winning sales pipeline with less effort. This is TQ.

You cannot manage what is not measured, yet not everything measured can be managed. Focus on the core activities or input metrics that make a difference and decide which skills to coach. You cannot succeed if you’re running blind or drowning in irrelevant data.

Sales management is typically the weak link in the revenue chain for most businesses.

Are new SDRs and sellers being onboarded in the effective use of their tools in the first thirty days? It’s not okay for reps to take six to nine months to be fully “ramped” in their roles.

As expensive field sales resources transition to inside sales at lower cost, and reliance on technology for digital outreach becomes the rule not the exception, TQ becomes table stakes to stay in the game. Outreach.io gets it: Triple your salesforce, without making a single hire.

Part II: Salesborg Action

The foundation of sales success is strong product/market fit, clarity concerning ideal customer profiles (ICPs), knowing your buyer personas, and then nailing your message and narrative with insightful questions!

Here is a summary of the power laws for effective outbound before you start thinking about enabling yourself with technology:

Your Value Narrative

All communication must be relentlessly about the target persona’s opportunity to drive improved results in their role. Do not open by talking about yourself, your company, your product, your service or your solution.

Be brief and communicate like a peer rather than a needy seller.

Relevant personalization is the force multiplier. As the legendary Marylou Tyler says, “Show them that you know them, right from the very beginning.”[2]

Provide genuine insights. Be confident yet humble. Be consultative but with a worthwhile point of view. Have a clear and simple call to action.

Steve W. Martin, a professor at USC who wrote the book Heavy Hitter Selling, highlights that C-level interactions actually work best when you humbly assume equal business stature (EBS).

In the digital age of selling, you must be able to write; otherwise you have a distinct disadvantage.

Crystal Knows uses AI to assess an individual’s personality to accurately predict their operating style and behaviors.

Be cautious of people who say they can predict the future, and welcome the people who suggest a model that can be tuned based on inputs to produce better results than random.

The enemy of every seller is false hope. The sooner you know where you really stand with a prospect, the better off you will be. Believe in your message and the value you provide even if they don’t become a customer.

It’s okay to be unfriended or deleted by people who are not going to buy.

One enabled sequencing master can eclipse a team of six, maybe even fifteen.

For top of funnel, applying high TQ gives you a huge advantage with:

  • Targeting.
  • Messaging.
  • Personalization.
  • Conversion.

Target for Relevance

A trigger event is something that creates buyer awareness concerning opportunity for change or the need for what we sell. It is important to understand that an attribute is not the same thing as a trigger.

Remember that attributes help define ICP and triggers equip you to have conversations within the right context with people in those organizations. The trigger event contextualizes why you are reaching out to the potential buyer now.

In our opinion, there are four types of trigger events relevant for sales:

  • Bad experience with incumbent suppliers.
  • Role-based change.
  • Change in results or strategy.
  • Operating environment changes.

In business-to-business sales, the most powerful trigger event is a decisionmaker role change because executives hired into new roles are expected to drive improvement.

Importantly, the key to working with trigger events is the use of technology. Triggr.ai is an excellent example. LeadIQ or Apollo.io are further examples of how you can also efficiently build lists based on trigger events.

The fastest path to a sale is found when combining trigger events with referrals.

Sales is a game of change management, and we must identify where the pain of the current state is greater than the pain of change.

In the land of laziness, fear and pain is the most effective motivator . . . sad but true.

If they don’t have any pain, a further conversation is likely a waste of time anyway, so “attention-getting personalization” that has nothing to do with the recipient’s needs can take everyone nowhere.

There are only four reasons to buy software and most other things in the world of business-to-business sales:

  • make money,
  • save money,
  • reduce risk or
  • maintain compliance.

Design, Test, Refine

The whole beauty of technology is that you can easily design A/B tests of subject lines right into a cadence in platforms such as Outreach.

If you launch twelve sequences, it would be great for the software itself to shift leads from one bucket into the other depending on how well they are doing.

Imagine the cadence list stack ranking the best sequences right in the UI!

Nova.ai is getting into the game using machine learning to auto-generate injectable snippets. Snippets are just a simple template you can load fast into an automated outbound set of email touches to personalize them to an individual prospect or persona or group of similar prospects within the ideal customer profile.

Tactical things to split test include:

  • time of day,
  • day of the week,
  • subject line length,
  • super short copy and long copy,
  • blends of short and long copy,
  • test all lowercase.

The sequencer of the future predicts the next best action.

The future of semi-automation will take into account an omni-channel perspective.

LinkedIn is always closing doors of automation to outsiders so it’s a tricky space to play.

Airborne is the first sales engagement platform designed and built for agencies: they solve multiple problems to make operations significantly more efficient. This includes managing multiple accounts, scheduling calls, setting up automated triggers, managing teams and keeping client data separate in secure silos.

In our experience, the best subject lines are one to three words. We prefer single action words like growth.

Sequences only work if you have the right message. Back up and make sure you’ve nailed your ICP, buyer personas, and relevant messaging.

Metrics

  • Open rates should be 30 to 50 percent at a minimum (ideally, you’re at 60 to 70 percent or more).
  • Reply rates should be 5 to 10 percent of total prospects contacted at a minimum.
  • At the end of the day, this is the most important metric. Conversion rates should be 3 to 6 percent of total prospects contacted at a minimum.

The average cold email response rate is 1 percent. The average success rate for a cold call is 1.48 percent.

Here is a summary of the REPLY methodology:

  • Relevant results. Prospects expect to see relevant results you’ve created for similar companies with similar challenges.
  • Empathy. Prospects want to feel understood.
  • Personalization. They expect personalized communication that shows your outreach was intended specifically for them.
  • Laser-focus. They expect brief, succinct communication.

Don’t be You-oriented (buyer-oriented). Make them the hero.

Outbound is an exercise in workflows and machine logic. The key is to nail the messaging at every touchpoint and master the technology that drives everything.

An important distinction for sellers is that it must be about “why they should care” not “why we do what we do”.

Here is sage sales copywriting advice from Shakespeare, da Vinci and Einstein:

  • “Brevity is the soul of wit.”  
  • “Simplicity is the ultimate sophistication.”

Become certified on as many platforms in this book that you can. XANT, SalesLoft, Outreach and Groove all have universities, online training and FAQs that go beyond the original onboarding sessions. Get certified on Salesforce Trailheads for Sales Operations.

The future of sales is a salesperson who speaks engineering, plain and simple.

All phone training should focus on tone and all outbound email should focus on imagery.

Eighty percent of email is visual, so you should use CloudApp and make mini feature explainer GIFs with wow or aha factor to capture the essence of your tech differentiation. Remember, you are trying to use visuals to pique interest.

While sequencing, make sure you consider inline explainer GIFs, Venn and Blast diagrams, comp analysis infographics, and anything visually short and sweet that will spike opens.

We humans are visual creatures and decide to buy on emotion and justify on logic.

A sequence is the order in which you execute multiple touches (message and channels). Cadence is the rhythm or frequency of the outreach. It pays to build out high touch sequences or flows depending on how involved you need to be with the prospect in your messaging before they will convert.

Inbound is less rejection-laden due to the prospect having attended an event, downloaded a white paper, requested a demo or quote, and so on. Yet inbound leads still demand persistence in order to secure engagement.

In deploying automation, you are seeking these outcomes: No, Not interested, Remove or Refer, and even the amazing Yes. If you are not assertive enough with the frequency of the sequence, they’ll sit on the fence forever with it. False hope and maybe is the killer of sales. A real no liberates you to focus where you can actually help someone else.

The best way to personalize currently is to segment your prospect base ABM / ABSD style. Lars Nilsson is an expert. He recommends you bucket them into personas and then build campaigns relevant per persona.

Automating Everything

You can tag up to six custom tags on your lead list in Navigator and re-sort the list almost like a CRM.

If you spam your entire TAM too quickly, you could burn out the known universe.

Technology is not just about mass automation with A/B testing, it is also for laser-focused effectiveness.

Outreach, SalesLoft, and XANT are all moving into AI and ML in different ways.

Someone living in a platform like Outreach for a year will outperform a brand-new user hands down. There is a significant learning curve for effective adoption and usage.

If you are able to use Orum, ConnectAndSell or ConnectLeader and go from five live conversations per day to twenty or even forty, you’ll need to know what to say.

The concept is ROUTE, RUIN, MULTIPLY.

The first question to ask is not: “Did I catch you at a bad time?”

Gong tested that as a baseline for opening and “How have you been?” far outperformed it.

Figure out who owns the problem in the company, and get routed or referred [ROUTE]. Figure out the incumbent and pull the string on whether they’re happy [RUIN]. Sell augmentation vs. rip and replace [MULTIPLY].

We’ve worked with nearly all the available data sources including ZoomInfo (which acquired DiscoverOrg, which had acquired RainKing), LeadIQ, Adapt.io, SalesIntel.io and Seamless.ai, Data.com, Lusha and Triggr.ai.

Leveraging intent data to contact the right person, at the right time, with the right message is powerful.

Bridge Group studies highlight that a great SDR can handle on average 200 accounts per month and be effective.

What’s the future of data platforms? With the ZoomInfo IPO in 2020, consolidation has gone berserk. Capital raising in the sales tech stack category is also rampant. Amidst all the offerings, when we think about gaps in what data providers offer, the glaring holes are normalization, enrichment, hygiene and the ability to smoothly ingest that signal into sales engagement platforms via. csv export/import automation.

Automation of data enrichment is important because customers and potential clients expect us to engage them on the basis that we:

  • truly know them,
  • personalize their experience and
  • anticipate their needs.

Working Your Systems

All responses are inherently positive. It’s a paradox. If someone has no interest whatsoever, they won’t even take the time to respond negatively.

Answer every single reply, negative or positive, and make sure you operate rapidly because speed of response makes a difference.

Revenue Grid takes nurturing automation seriously — the tool allows you to create automation rules, especially for account nurturing.

When we’re monitoring and optimizing large-scale outbound campaigns, we always look for something we’ve dubbed “signs of life”.

Social platforms, especially LinkedIn, are gold mines for finding context for your outreach.

Never “connect and sell” on social platforms. First connect and provide some form of value (share their article, provide positive commentary, give them a genuine white paper or industry report relevant to them and not about you).

Blend physical world tactics with digital engagement.

Craig Elias focuses on three types of trigger events: awareness, bad supplier and job changes. The vast majority of Outreach or SalesLoft sequences are awareness messages or specious ROI claims such as: “Drive revenue by 234 percent!”

Craig claims the average CXO makes buying decisions early in their new role, shaking up the status quo when they join the new organization. Get in early.

A referral — a common trusted relationship endorsing you — is the most powerful way to open because there is a level of trust.

Trigger events and referrals together are like a sales superpower because they transform sales results and they make the sales process much easier than cold calling or sending generic emails.

The company that figures out how to programmatically scale warm referrals will be a billion-dollar unicorn. Cosell.io looks promising.

The future of B2B is paid micro communities within platforms such as Slack, Patreon or Discord where membership criteria controls the quality of the vendors placed in front of the CXO.

Join think tanks, collectives and societies that help you cross-sell with other sales leaders in your vertical.

That includes Revenue Collective, Sales Enablement Society, WizOps, Sales IQ, RevGenius, SalesStack.io, SDRevolution, SDReady and Modern Sales Pros (MSP).

Knowing your ICP is how you identify and size your TAM (Total/Target Addressable Market) and then knowing your buyer personas and engaging based on trigger events or trusted relationships is how you maximize sales results.

Psychographics explain how the leadership in an organization thinks, feels and acts. Psychographics provide insights into what they value and what motivates them to buy.

Customers in growth mode are seeking to improve efficiency, grow revenue, expand markets, drive loyalty and so on. Growth often indicates openness to change and a willingness to invest in improving operations and financial performance.

ICP is about identifying the attributes of organizations with the highest likelihood of engaging with you in conversations about changing away from your competitor or away from the status quo.

Take your time to define your ICP. Build at least three to five buyer personas and title cloud arrays. Hone in on the stories of similar customers for each persona. Understand the challenges, trends, and drivers in their industry.

A buyer persona is a summary of the archetype buyer role to whom you sell.

According to Marylou Tyler: “Being able to reduce sales cycles and increase conversion rates depends on knowing who the buyers are, what they care about, what results they are looking for, and how they communicate.”[3]

A buyer persona needs to capture demographics, goals, and objectives in how they are measured in their role. It also needs to capture key areas of focus, challenges and problems, sources of influence, phrases that resonate, objections to anticipate and proof of results we enable (reference customers). Most importantly: Why change, why now, and why with you?

You’re not enabled as a seller without killer ICP and buyer persona documentation.

Powering Up

Do the hard work with ICP, buyer personas, TAM and messaging before talking to an agency, then challenge them to add value and prove they can deliver results without damaging your brand.

The future is a virtual assistance bot that books your meetings, confirms appointments, prompts you on outstanding tasks and more.

Talking the language of leaders (desired outcomes and compelling business case).

Outreach, SalesLoft and XANT all operate like adding a couple of SDRs if you work on your TQ and master the messaging and systems. Otherwise, just like Sales Navigator, these things become AFL: another frickin’ login. Most sales tech is like an expensive gym membership . . . you pay every month and hardly ever use it.

It is essential that they can tie all the systems together such as Sales Navigator (social) + data + sequencer + phone, and execute in ways that are consistent with your own style and brand for seamless handoffs.

Chili Piper is hands down, far and away, the most effective scheduling software for sellers.

Dare to be different linguistically. Cognitive dissonance is real. If content is bizarre, it will get read . . . just don’t damage your brand!

Curious people with the right values go through hell to understand another person’s business. They actively listen to cultivate curiosity on both sides, and this is fundamentally important.

If you leverage intelligent automation for top of funnel and other repetitive tasks, you can then focus on where there is alignment rather than pressure for a close.

You cannot be hungry, needy or pushy — nor lose your cool when anyone accuses you of spamming them.

An outside sales call costs up to six times more than an inside sales call.

Luigi Prestinenzi from Sales IQ often asks business leaders or the VP of Sales similar questions: “What’s the average cost per lead from marketing versus sales self – generated by reps?” He follows up with: “What’s the conversion rate from each channel?” Then the knock-out combination: “How many of your reps are on target year-to-date?” A thoughtful pause: “Hmm . . . what’s the gap costing you in revenue and what’s the impact of not fixing this for you and the business?”[4]

The truth of the matter for complex enterprise selling is that semi-automation is the best we can achieve right now.

Strive for hyper-short subject lines with just one to three words with one being an action word. Strive for three to five sentences maximum in the email, with a CTA as the third. Use pattern interrupts and make what you say stick out. Be novel in word choice. Be assumptive without being arrogant. Make the personalization about the relevant pain rather than vanilla demographic, psychographic or technographic information.

There is a new category emerging: sales ops for SEPs (sales engagement platforms), sometimes just called sequencers.

A big issue for all sales automation is data governance on prospects, whether it’s handling GDPR/CCPA compliance to something as simple as suppression lists, or handling DNC and permissions across your system of record (CRM) and system of engagement (SEP) including Outreach, SalesLoft and XANT.

Leaders love brevity, and any app that forces others to be brief is favored.

In the not-too-distant future, private Slack Communities will emerge where vendors pay an entry fee or per interaction to be paired with the optimal decisionmakers. The host mediator (could be an AI) will play matchmaker. We will move into a post-email world in the not-too-distant future.

Twitter is most powerful for monitoring the activity of any target prospect and quickly creating engagement or awareness so that your outreach is anything but cold. Treat Twitter as a trigger event monitoring platform and then use it to direct – message them, just like sending an SMS (text message) to their phone or WhatsApp message.

Back in the 2010s, business focused on specializing sales team roles for the Henry Ford production line of selling. An SDR should focus on sourcing new leads and AEs should work opportunities to close deals, often working with technical pre-sales specialists.

Driving Sales Success

OAC rate varies depending on the size of companies you’re targeting. And thus, the number of companies you can reach out to on a monthly basis. That said, If you’re within 1.5 to 10 percent, you’re in a great place. When it comes to outbound contact conversion (OCC), if you’re within 0.5 to 2.5 percent for your OCC rate, you’re in a great place.

To again quote Anthony Iannarino : “Opening is the new closing.”[5]

You cannot be a great opener if you cannot close for an initial commitment of time, and qualification and discovery information — that’s the way the paradox all fits together.

Closing sales is just the act of securing another commitment, the commitment to buy it, which is not too dissimilar to closing on the first commitment, which is the agreement to give you their time and information for discovery and qualification. There is no such thing as a good opener and a good closer.

Many AEs are just pedestrian account managers closing the occasional new deal . . . enough not to get fired but not enough to be successful.

SDRs should always respond quickly to all the outbound replies and assiduously follow up to make sure they are sending the AE the names of “high opens” and referrals so the AE can triple them (call, vmail, email in under ninety seconds).

Salesforce has introduced High Velocity Sales (HVS) to rival SalesLoft and Outreach natively within their platform, and it is powered by Einstein AI for recommended best next steps.

In Sales Navigator you can share lead lists with another member on the team. Shared Accounts and Targeted Lead Lists are so powerful to cowork the social patch! Simple innovation, very deep practical application and high ROI.

The videoconference category is rife for disruption post-pandemic to let its proverbial hair down.

Chris Beall believes that one phone conversation is worth 240 email interactions. The neuroscience concerning image-processing versus text reveals a single image is worth 60,000 words.

It astounds us when we consider how many sellers just have no idea about the basics when it comes to selling virtually. Problems include having an unrecognizable face because the lighting is wrong, rubbish audio with a hopeless microphone, variable annoying audio levels, looking up a person’s nostrils, double chin and ceiling as they talk down to us. We could go on, and failures in this area are enough to get someone fired.

ABP = always be prospecting, always be sending out sequences, always be operating asynchronously.

Technology allows us to relax while appearing to be always on and hyper-responsive, even superhuman. This is especially true for account managers and CSMs.

Account – based selling (ABS) and the customer success manager (CSM) roles are massively important in a recession because new clients are even tougher to acquire than in good times.

When you’re managing a client, you’re responsible for troubleshooting issues, finding areas of opportunity, leveraging long-term partnerships, often while being measured on satisfaction and promoter scores using metrics such as NPS.

The KPIs for a CSM often include coverage of accounts, connected calls, renewals and new revenue, contract terms, and most important, net churn.

Role-based trigger events are insanely powerful for CSMs and account managers.

Successful CSMs are not “professional visitors” but instead are trusted consultative partners, aligning with the customer’s strategy and priorities.

Consider platforms such as Ultimate.ai that automates up to 80 percent of customer support interactions.

Relationships have always mattered.

In complex enterprise selling and account management, success depends on knowing “proof of life” in relationships and mapping the real economic and political power base within and between organizations.

The collective Social Capital of an organization is one of the most under-utilized and undervalued assets an organization has. It is rarely systematically leveraged, particularly by large enterprises.

The automation of relationship intelligence through relationship analytics is also important because it can rapidly and reliably detect powerful trigger events that signal both opportunity and threat within an account.

Engagement, application and accountability are keys to effective sales enablement. When it comes to developing TQ, you must immerse yourself in the tools within your stack.

You need to know where all the buttons are, integrations and advanced features. Be technically curious, figure out how to use snippets, rulesets and custom fields, placeholders, merge fields and templates.

The sequencers (SEPs) are the next Salesforce, Hubspot and Marketo for sales pipeline creation.

Learning tech stacks is just like the software demo process — it’s about the repetitions needed to become good, and then, with practice, masterful.

B2B marketing and sales leaders must provide reskilling and upskilling training so sellers can keep pace with current and future buyers.

Once any business grows above $ 20 to $ 30 million, fully commit to investing in all the power tools and even third – party consultants to drive growth with a killer machine of sales and marketing automation, augmented with the best specialist humans for insightful engagement.

Three hidden keys for managers and reps to drive sales pipeline in a crisis. These are empathy, humanization, and personalization.

The new normal emerged in the back end of 2020 with harsh economic realities. Sellers who are unable to cocreate a vision for a better future with their clients, and then nail the business case for the customer investing, are in trouble.

We are in the age of the machines, where the bots may reign supreme. Here are essential skills needed to survive and thrive in these new times: Go beyond IQ and EQ to now have TQ with superhuman levels of effectiveness.

Have empathy and insight in providing real value in conversations that lead to, not lead with the product, service, or solution you sell.

Become a masterful digital seller.

Part III: The Future of Selling

A Day in the Life of Tomorrow

Meetings became shorter online and with less real emotional connection.

Buyers adopted a harder stance: “Don’t sell to us and create unnecessary relationship overhead. Instead, prove your relevance and value before we decide whether to invest in any real face-to-face meetings.”

We believe one-third of current field sales roles will disappear in the 2020s.

Empathy combined with business acumen and an insight-laden consultative approach is now a mandatory requirement in the field.

What the not-too-distant future looks like for B2B sales, let’s see what the Chief Strategy Officer at XANT, Dave Boyce, believes are the major trends:

  • The customer of the future controls when and how she interacts with salespeople.
  • The modern sales rep can do everything from her desk. Meetings are held remotely, approvals are secured remotely, signatures are delivered remotely. The modern sales rep spends in-person time with her customers only at their request, and sometimes not until after the purchase.
  • When it comes to AI for sales, it matters which type of AI. If you want to optimize words, use conversational AI. If you want to optimize process, use process AI. If you want to work on the right things — the things that will convert to sales — you must use behavioral AI.
  • To email prospecting – The key is prioritization — which accounts, which people, when, and how?

Digital selling will evolve just like every other business application space.

  • First, automation.
  • Next, intelligence.
  • Finally, eCommerce.

Beyond their relationship skills, reps will succeed based on their ability to understand and interpret data, work effectively with AI, and move quickly on opportunities. That’s a very different sales profile from the one many companies recruit for today.

Is a data scientist the rep of the future?

Here are our twenty predictions for B2B selling in the roaring 2020s:

  • Remote working and virtual selling become the norm as the war for sales talent changes.
  • Revenue operations (RevOps), incorporating sales operations, reports directly to the CEO.
  • The rise of mega inside sales tech stacks.
  • The investment and op-ex mix for sales and marketing swings from salaries toward technology.
  • Channel-shift strategies mature to move prospect and customer engagement to automation.
  • The decade finishes with 33 percent fewer field salespeople.
  • Five billion dollars in VC capital goes into sales tech tools creating a Cambrian explosion of sales technology.
  • By 2025, a startup proves it is successfully running “SDR ex Machina” with fully autonomous top funnel and closing.
  • By 2027, digital virtual sales assistants (DVSAs) are a real thing.
  • Having already passed the Turing test on the phone and text-based chat, Sales AI passes the Turing test on a Zoom call.
  • AI automated email and sales outreach becomes regulated by the Federal Trade Commission (FTC).
  • Government regulators around the world ban deceptive fake human outreach on video or phone.
  • CRM morphs into full-blown customer experience (CX) and the segment stratifies with two gorillas dominating the market, Salesforce and Microsoft, followed by Hubspot.
  • CRM cloud wars heat up with an avalanche of acquisitions.
  • Sales management returns to the age of innocence.
  • Sales enablement focuses on eLearning and virtual engagement.
  • AI bots buy and sell to each other at the speed of high-frequency trading.
  • Mega corporations dominate.
  • The socioeconomic divide magnifies with salaries for skilled workers going backward while unemployment hits record levels.
  • The Singularity horizon comes into sight along with a resurgence in debates about values, purpose and meaning.

Can a salesbot really replace a human? Yes, if the buyer is seeking a commodity. It’s already happening.

The meta-skills that save humans in a sales career are empathy, insight and storytelling — they are how you create emotional connection to transfer belief and build trust.

As you think about your future in sales, don’t confuse job with task. Your job is safe if you automate as many tasks as possible.

Change is an opportunity for those with the right mindset.


[1] In the book on page 18

[2] In the book on page 54

[3] In the book on page 136

[4] In the book on page 158

[5] In the book on page 169

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